diff --git a/.claude/settings.json b/.claude/settings.json
new file mode 100644
index 0000000000..ac6b69b143
--- /dev/null
+++ b/.claude/settings.json
@@ -0,0 +1,34 @@
+{
+  "permissions": {
+    "allow": [
+      "Bash(find:*)",
+      "Bash(ls:*)",
+      "Bash(git:*)",
+      "Bash(git status:*)",
+      "Bash(git log:*)",
+      "Bash(git diff:*)",
+      "Bash(git show:*)",
+      "Bash(git branch:*)",
+      "Bash(git remote:*)",
+      "Bash(git tag:*)",
+      "Bash(git stash list:*)",
+      "Bash(git rev-parse:*)",
+      "Bash(gh pr view:*)",
+      "Bash(gh pr list:*)",
+      "Bash(gh pr checks:*)",
+      "Bash(gh pr diff:*)",
+      "Bash(gh issue view:*)",
+      "Bash(gh issue list:*)",
+      "Bash(gh run view:*)",
+      "Bash(gh run list:*)",
+      "Bash(gh run logs:*)",
+      "Bash(gh repo view:*)",
+      "WebFetch(domain:github.com)",
+      "WebFetch(domain:docs.sentry.io)",
+      "WebFetch(domain:develop.sentry.dev)",
+      "Bash(grep:*)",
+      "Bash(mv:*)"
+    ],
+    "deny": []
+  }
+}
diff --git a/.craft.yml b/.craft.yml
index 665f06834a..ea98f2d402 100644
--- a/.craft.yml
+++ b/.craft.yml
@@ -1,4 +1,4 @@
-minVersion: 0.34.1
+minVersion: 2.17.0
 targets:
   - name: pypi
     includeNames: /^sentry[_\-]sdk.*$/
diff --git a/.git-blame-ignore-revs b/.git-blame-ignore-revs
index 8efbe19ec3..e354c1ed92 100644
--- a/.git-blame-ignore-revs
+++ b/.git-blame-ignore-revs
@@ -2,3 +2,4 @@
 afea4a017bf13f78e82f725ea9d6a56a8e02cb34
 23a340a9dca60eea36de456def70c00952a33556
 973dda79311cf6b9cb8f1ba67ca0515dfaf9f49c
+e275c9e94323b429f39196881fb992d81a2e52ea
diff --git a/.github/release.yml b/.github/release.yml
index 058bc4d5bb..4383f70e7d 100644
--- a/.github/release.yml
+++ b/.github/release.yml
@@ -10,23 +10,28 @@ changelog:
         - "Changelog: Feature"
       commit_patterns:
         - "^feat\\b"
+      semver: minor
     - title: Bug Fixes 🐛
       labels:
         - "Changelog: Bugfix"
       commit_patterns:
         - "^(fix|bugfix)\\b"
+      semver: patch
     - title: Deprecations 🏗️
       labels:
         - "Changelog: Deprecation"
       commit_patterns:
         - "deprecat"  # deprecation, deprecated
+      semver: patch
     - title: Documentation 📚
       labels:
         - "Changelog: Docs"
       commit_patterns:
         - "^docs?\\b"
+      semver: patch
     - title: Internal Changes 🔧
       labels:
         - "Changelog: Internal"
       commit_patterns:
         - "^(build|ref|chore|ci|tests?)\\b"
+      semver: patch
diff --git a/.github/workflows/ai-integration-test.yml b/.github/workflows/ai-integration-test.yml
new file mode 100644
index 0000000000..bd1f1c6f85
--- /dev/null
+++ b/.github/workflows/ai-integration-test.yml
@@ -0,0 +1,45 @@
+name: AI integration tests
+
+on:
+  workflow_dispatch:
+  schedule:
+    # every weekday
+    - cron: '23 3 * * 1-5'
+
+jobs:
+  ai-integration-tests:
+    name: AI integration tests
+    runs-on: ubuntu-latest
+    environment: "AI Integrations Tests"
+    timeout-minutes: 10
+
+    permissions:
+      contents: write
+      issues: write
+
+    steps:
+      - name: Setup Python
+        uses: actions/setup-python@v6
+        with:
+          python-version: 3.14t
+
+      - name: Setup Node.js
+        uses: actions/setup-node@v6
+        with:
+          node-version: '20'
+
+      - name: Checkout repo
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
+        with:
+          token: ${{ secrets.GITHUB_TOKEN }}
+
+      - name: Run Python SDK Tests
+        uses: getsentry/testing-ai-sdk-integrations@dba21cbfb57482556338983d8c35e6b09b534667
+        env:
+          GITHUB_TOKEN: ${{ secrets.GITHUB_TOKEN }}
+        with:
+          language: py
+          sentry-python-path: ${{ github.workspace }}
+          openai-api-key: ${{ secrets.OPENAI_API_KEY }}
+          anthropic-api-key: ${{ secrets.ANTHROPIC_API_KEY }}
+          google-api-key:  ${{ secrets.GOOGLE_API_KEY }}
diff --git a/.github/workflows/changelog-preview.yml b/.github/workflows/changelog-preview.yml
new file mode 100644
index 0000000000..3788b29609
--- /dev/null
+++ b/.github/workflows/changelog-preview.yml
@@ -0,0 +1,19 @@
+name: Changelog Preview
+on:
+  pull_request_target:
+    types:
+    - opened
+    - synchronize
+    - reopened
+    - edited
+    - labeled
+    - unlabeled
+permissions:
+  contents: write
+  pull-requests: write
+  statuses: write
+
+jobs:
+  changelog-preview:
+    uses: getsentry/craft/.github/workflows/changelog-preview.yml@v2
+    secrets: inherit
diff --git a/.github/workflows/ci.yml b/.github/workflows/ci.yml
index 44fe331b34..c3fc1ae316 100644
--- a/.github/workflows/ci.yml
+++ b/.github/workflows/ci.yml
@@ -24,7 +24,7 @@ jobs:
     timeout-minutes: 10
 
     steps:
-      - uses: actions/checkout@v6.0.1
+      - uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
       - uses: actions/setup-python@v6
         with:
           python-version: 3.14
@@ -39,7 +39,7 @@ jobs:
     timeout-minutes: 10
 
     steps:
-      - uses: actions/checkout@v6.0.1
+      - uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
       - uses: actions/setup-python@v6
         with:
           python-version: 3.12
@@ -70,7 +70,7 @@ jobs:
     timeout-minutes: 10
 
     steps:
-      - uses: actions/checkout@v6.0.1
+      - uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
       - uses: actions/setup-python@v6
         with:
           python-version: 3.12
diff --git a/.github/workflows/codeql-analysis.yml b/.github/workflows/codeql-analysis.yml
index 79af0a3039..a8f3e199bd 100644
--- a/.github/workflows/codeql-analysis.yml
+++ b/.github/workflows/codeql-analysis.yml
@@ -48,7 +48,7 @@ jobs:
 
     steps:
     - name: Checkout repository
-      uses: actions/checkout@v6.0.1
+      uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
 
     # Initializes the CodeQL tools for scanning.
     - name: Initialize CodeQL
diff --git a/.github/workflows/release-comment-issues.yml b/.github/workflows/release-comment-issues.yml
index 8870f25bc0..e18aeab155 100644
--- a/.github/workflows/release-comment-issues.yml
+++ b/.github/workflows/release-comment-issues.yml
@@ -10,6 +10,11 @@ on:
         required: false
 
 # This workflow is triggered when a release is published
+permissions:
+  issues: write
+  contents: write
+  pull-requests: write
+
 jobs:
   release-comment-issues:
     runs-on: ubuntu-20.04
diff --git a/.github/workflows/release.yml b/.github/workflows/release.yml
index a5b89d2734..fe56354e7d 100644
--- a/.github/workflows/release.yml
+++ b/.github/workflows/release.yml
@@ -1,38 +1,40 @@
 name: Release
-
 on:
   workflow_dispatch:
     inputs:
       version:
-        description: Version to release
-        required: true
+        description: Version to release (or "auto")
+        required: false
       force:
-        description: Force a release even when there are release-blockers (optional)
+        description: Force a release even when there are release-blockers
         required: false
       merge_target:
-        description: Target branch to merge into. Uses the default branch as a fallback (optional)
+        description: Target branch to merge into
         required: false
+permissions:
+  contents: write
+  pull-requests: write
 
 jobs:
   release:
     runs-on: ubuntu-latest
-    name: "Release a new version"
+    name: Release a new version
     steps:
-      - name: Get auth token
-        id: token
-        uses: actions/create-github-app-token@29824e69f54612133e76f7eaac726eef6c875baf # v2.2.1
-        with:
-          app-id: ${{ vars.SENTRY_RELEASE_BOT_CLIENT_ID }}
-          private-key: ${{ secrets.SENTRY_RELEASE_BOT_PRIVATE_KEY }}
-      - uses: actions/checkout@v6.0.1
-        with:
-          token: ${{ steps.token.outputs.token }}
-          fetch-depth: 0
-      - name: Prepare release
-        uses: getsentry/action-prepare-release@v1
-        env:
-          GITHUB_TOKEN: ${{ steps.token.outputs.token }}
-        with:
-          version: ${{ github.event.inputs.version }}
-          force: ${{ github.event.inputs.force }}
-          merge_target: ${{ github.event.inputs.merge_target }}
+    - name: Get auth token
+      id: token
+      uses: actions/create-github-app-token@29824e69f54612133e76f7eaac726eef6c875baf # v2
+      with:
+        app-id: ${{ vars.SENTRY_RELEASE_BOT_CLIENT_ID }}
+        private-key: ${{ secrets.SENTRY_RELEASE_BOT_PRIVATE_KEY }}
+    - uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6
+      with:
+        token: ${{ steps.token.outputs.token }}
+        fetch-depth: 0
+    - name: Prepare release
+      uses: getsentry/craft@beea4aba589c66381258cbd131c5551ae8245b82 # v2
+      env:
+        GITHUB_TOKEN: ${{ steps.token.outputs.token }}
+      with:
+        version: ${{ inputs.version }}
+        force: ${{ inputs.force }}
+        merge_target: ${{ inputs.merge_target }}
diff --git a/.github/workflows/test-integrations-agents.yml b/.github/workflows/test-integrations-agents.yml
index e2be8508ea..a05649a5f0 100644
--- a/.github/workflows/test-integrations-agents.yml
+++ b/.github/workflows/test-integrations-agents.yml
@@ -17,6 +17,9 @@ concurrency:
   cancel-in-progress: true
 permissions:
   contents: read
+  actions: read
+  pull-requests: write
+  statuses: write
 env:
   BUILD_CACHE_KEY: ${{ github.sha }}
   CACHED_BUILD_PATHS: |
@@ -38,7 +41,7 @@ jobs:
     # Use Docker container only for Python 3.6
     container: ${{ matrix.python-version == '3.6' && 'python:3.6' || null }}
     steps:
-      - uses: actions/checkout@v6.0.1
+      - uses: actions/checkout@v6.0.2
       - uses: actions/setup-python@v6
         if: ${{ matrix.python-version != '3.6' }}
         with:
@@ -69,21 +72,13 @@ jobs:
         run: |
           coverage combine .coverage-sentry-*
           coverage xml
-      - name: Upload coverage to Codecov
+      - name: Parse and Upload Coverage
         if: ${{ !cancelled() }}
-        uses: codecov/codecov-action@v5.5.2
+        uses: getsentry/codecov-action@main
         with:
-          token: ${{ secrets.CODECOV_TOKEN }}
+          token: ${{ secrets.GITHUB_TOKEN }}
           files: coverage.xml
-          # make sure no plugins alter our coverage reports
-          plugins: noop
-          verbose: true
-      - name: Upload test results to Codecov
-        if: ${{ !cancelled() }}
-        uses: codecov/test-results-action@v1
-        with:
-          token: ${{ secrets.CODECOV_TOKEN }}
-          files: .junitxml
+          junit-xml-pattern: .junitxml
           verbose: true
   check_required_tests:
     name: All Agents tests passed
diff --git a/.github/workflows/test-integrations-ai-workflow.yml b/.github/workflows/test-integrations-ai-workflow.yml
index d641becd25..7cd4cb86df 100644
--- a/.github/workflows/test-integrations-ai-workflow.yml
+++ b/.github/workflows/test-integrations-ai-workflow.yml
@@ -17,6 +17,9 @@ concurrency:
   cancel-in-progress: true
 permissions:
   contents: read
+  actions: read
+  pull-requests: write
+  statuses: write
 env:
   BUILD_CACHE_KEY: ${{ github.sha }}
   CACHED_BUILD_PATHS: |
@@ -38,7 +41,7 @@ jobs:
     # Use Docker container only for Python 3.6
     container: ${{ matrix.python-version == '3.6' && 'python:3.6' || null }}
     steps:
-      - uses: actions/checkout@v6.0.1
+      - uses: actions/checkout@v6.0.2
       - uses: actions/setup-python@v6
         if: ${{ matrix.python-version != '3.6' }}
         with:
@@ -73,21 +76,13 @@ jobs:
         run: |
           coverage combine .coverage-sentry-*
           coverage xml
-      - name: Upload coverage to Codecov
+      - name: Parse and Upload Coverage
         if: ${{ !cancelled() }}
-        uses: codecov/codecov-action@v5.5.2
+        uses: getsentry/codecov-action@main
         with:
-          token: ${{ secrets.CODECOV_TOKEN }}
+          token: ${{ secrets.GITHUB_TOKEN }}
           files: coverage.xml
-          # make sure no plugins alter our coverage reports
-          plugins: noop
-          verbose: true
-      - name: Upload test results to Codecov
-        if: ${{ !cancelled() }}
-        uses: codecov/test-results-action@v1
-        with:
-          token: ${{ secrets.CODECOV_TOKEN }}
-          files: .junitxml
+          junit-xml-pattern: .junitxml
           verbose: true
   check_required_tests:
     name: All AI Workflow tests passed
diff --git a/.github/workflows/test-integrations-ai.yml b/.github/workflows/test-integrations-ai.yml
index fc1a9f7b90..0b305a3775 100644
--- a/.github/workflows/test-integrations-ai.yml
+++ b/.github/workflows/test-integrations-ai.yml
@@ -17,6 +17,9 @@ concurrency:
   cancel-in-progress: true
 permissions:
   contents: read
+  actions: read
+  pull-requests: write
+  statuses: write
 env:
   BUILD_CACHE_KEY: ${{ github.sha }}
   CACHED_BUILD_PATHS: |
@@ -38,7 +41,7 @@ jobs:
     # Use Docker container only for Python 3.6
     container: ${{ matrix.python-version == '3.6' && 'python:3.6' || null }}
     steps:
-      - uses: actions/checkout@v6.0.1
+      - uses: actions/checkout@v6.0.2
       - uses: actions/setup-python@v6
         if: ${{ matrix.python-version != '3.6' }}
         with:
@@ -89,21 +92,13 @@ jobs:
         run: |
           coverage combine .coverage-sentry-*
           coverage xml
-      - name: Upload coverage to Codecov
+      - name: Parse and Upload Coverage
         if: ${{ !cancelled() }}
-        uses: codecov/codecov-action@v5.5.2
+        uses: getsentry/codecov-action@main
         with:
-          token: ${{ secrets.CODECOV_TOKEN }}
+          token: ${{ secrets.GITHUB_TOKEN }}
           files: coverage.xml
-          # make sure no plugins alter our coverage reports
-          plugins: noop
-          verbose: true
-      - name: Upload test results to Codecov
-        if: ${{ !cancelled() }}
-        uses: codecov/test-results-action@v1
-        with:
-          token: ${{ secrets.CODECOV_TOKEN }}
-          files: .junitxml
+          junit-xml-pattern: .junitxml
           verbose: true
   check_required_tests:
     name: All AI tests passed
diff --git a/.github/workflows/test-integrations-cloud.yml b/.github/workflows/test-integrations-cloud.yml
index d655af0a1a..d57034d4e3 100644
--- a/.github/workflows/test-integrations-cloud.yml
+++ b/.github/workflows/test-integrations-cloud.yml
@@ -17,6 +17,9 @@ concurrency:
   cancel-in-progress: true
 permissions:
   contents: read
+  actions: read
+  pull-requests: write
+  statuses: write
 env:
   BUILD_CACHE_KEY: ${{ github.sha }}
   CACHED_BUILD_PATHS: |
@@ -42,7 +45,7 @@ jobs:
     # Use Docker container only for Python 3.6
     container: ${{ matrix.python-version == '3.6' && 'python:3.6' || null }}
     steps:
-      - uses: actions/checkout@v6.0.1
+      - uses: actions/checkout@v6.0.2
       - uses: actions/setup-python@v6
         if: ${{ matrix.python-version != '3.6' }}
         with:
@@ -85,21 +88,13 @@ jobs:
         run: |
           coverage combine .coverage-sentry-*
           coverage xml
-      - name: Upload coverage to Codecov
+      - name: Parse and Upload Coverage
         if: ${{ !cancelled() }}
-        uses: codecov/codecov-action@v5.5.2
+        uses: getsentry/codecov-action@main
         with:
-          token: ${{ secrets.CODECOV_TOKEN }}
+          token: ${{ secrets.GITHUB_TOKEN }}
           files: coverage.xml
-          # make sure no plugins alter our coverage reports
-          plugins: noop
-          verbose: true
-      - name: Upload test results to Codecov
-        if: ${{ !cancelled() }}
-        uses: codecov/test-results-action@v1
-        with:
-          token: ${{ secrets.CODECOV_TOKEN }}
-          files: .junitxml
+          junit-xml-pattern: .junitxml
           verbose: true
   check_required_tests:
     name: All Cloud tests passed
diff --git a/.github/workflows/test-integrations-common.yml b/.github/workflows/test-integrations-common.yml
index b87b8e56d2..9b333435bd 100644
--- a/.github/workflows/test-integrations-common.yml
+++ b/.github/workflows/test-integrations-common.yml
@@ -17,6 +17,9 @@ concurrency:
   cancel-in-progress: true
 permissions:
   contents: read
+  actions: read
+  pull-requests: write
+  statuses: write
 env:
   BUILD_CACHE_KEY: ${{ github.sha }}
   CACHED_BUILD_PATHS: |
@@ -38,7 +41,7 @@ jobs:
     # Use Docker container only for Python 3.6
     container: ${{ matrix.python-version == '3.6' && 'python:3.6' || null }}
     steps:
-      - uses: actions/checkout@v6.0.1
+      - uses: actions/checkout@v6.0.2
       - uses: actions/setup-python@v6
         if: ${{ matrix.python-version != '3.6' }}
         with:
@@ -65,21 +68,13 @@ jobs:
         run: |
           coverage combine .coverage-sentry-*
           coverage xml
-      - name: Upload coverage to Codecov
+      - name: Parse and Upload Coverage
         if: ${{ !cancelled() }}
-        uses: codecov/codecov-action@v5.5.2
+        uses: getsentry/codecov-action@main
         with:
-          token: ${{ secrets.CODECOV_TOKEN }}
+          token: ${{ secrets.GITHUB_TOKEN }}
           files: coverage.xml
-          # make sure no plugins alter our coverage reports
-          plugins: noop
-          verbose: true
-      - name: Upload test results to Codecov
-        if: ${{ !cancelled() }}
-        uses: codecov/test-results-action@v1
-        with:
-          token: ${{ secrets.CODECOV_TOKEN }}
-          files: .junitxml
+          junit-xml-pattern: .junitxml
           verbose: true
   check_required_tests:
     name: All Common tests passed
diff --git a/.github/workflows/test-integrations-dbs.yml b/.github/workflows/test-integrations-dbs.yml
index 4638525be7..b1dadb0ca5 100644
--- a/.github/workflows/test-integrations-dbs.yml
+++ b/.github/workflows/test-integrations-dbs.yml
@@ -17,6 +17,9 @@ concurrency:
   cancel-in-progress: true
 permissions:
   contents: read
+  actions: read
+  pull-requests: write
+  statuses: write
 env:
   BUILD_CACHE_KEY: ${{ github.sha }}
   CACHED_BUILD_PATHS: |
@@ -56,7 +59,7 @@ jobs:
     # Use Docker container only for Python 3.6
     container: ${{ matrix.python-version == '3.6' && 'python:3.6' || null }}
     steps:
-      - uses: actions/checkout@v6.0.1
+      - uses: actions/checkout@v6.0.2
       - uses: actions/setup-python@v6
         if: ${{ matrix.python-version != '3.6' }}
         with:
@@ -105,21 +108,13 @@ jobs:
         run: |
           coverage combine .coverage-sentry-*
           coverage xml
-      - name: Upload coverage to Codecov
+      - name: Parse and Upload Coverage
         if: ${{ !cancelled() }}
-        uses: codecov/codecov-action@v5.5.2
+        uses: getsentry/codecov-action@main
         with:
-          token: ${{ secrets.CODECOV_TOKEN }}
+          token: ${{ secrets.GITHUB_TOKEN }}
           files: coverage.xml
-          # make sure no plugins alter our coverage reports
-          plugins: noop
-          verbose: true
-      - name: Upload test results to Codecov
-        if: ${{ !cancelled() }}
-        uses: codecov/test-results-action@v1
-        with:
-          token: ${{ secrets.CODECOV_TOKEN }}
-          files: .junitxml
+          junit-xml-pattern: .junitxml
           verbose: true
   check_required_tests:
     name: All DBs tests passed
diff --git a/.github/workflows/test-integrations-flags.yml b/.github/workflows/test-integrations-flags.yml
index 9c3c647937..dded26658a 100644
--- a/.github/workflows/test-integrations-flags.yml
+++ b/.github/workflows/test-integrations-flags.yml
@@ -17,6 +17,9 @@ concurrency:
   cancel-in-progress: true
 permissions:
   contents: read
+  actions: read
+  pull-requests: write
+  statuses: write
 env:
   BUILD_CACHE_KEY: ${{ github.sha }}
   CACHED_BUILD_PATHS: |
@@ -38,7 +41,7 @@ jobs:
     # Use Docker container only for Python 3.6
     container: ${{ matrix.python-version == '3.6' && 'python:3.6' || null }}
     steps:
-      - uses: actions/checkout@v6.0.1
+      - uses: actions/checkout@v6.0.2
       - uses: actions/setup-python@v6
         if: ${{ matrix.python-version != '3.6' }}
         with:
@@ -77,21 +80,13 @@ jobs:
         run: |
           coverage combine .coverage-sentry-*
           coverage xml
-      - name: Upload coverage to Codecov
+      - name: Parse and Upload Coverage
         if: ${{ !cancelled() }}
-        uses: codecov/codecov-action@v5.5.2
+        uses: getsentry/codecov-action@main
         with:
-          token: ${{ secrets.CODECOV_TOKEN }}
+          token: ${{ secrets.GITHUB_TOKEN }}
           files: coverage.xml
-          # make sure no plugins alter our coverage reports
-          plugins: noop
-          verbose: true
-      - name: Upload test results to Codecov
-        if: ${{ !cancelled() }}
-        uses: codecov/test-results-action@v1
-        with:
-          token: ${{ secrets.CODECOV_TOKEN }}
-          files: .junitxml
+          junit-xml-pattern: .junitxml
           verbose: true
   check_required_tests:
     name: All Flags tests passed
diff --git a/.github/workflows/test-integrations-gevent.yml b/.github/workflows/test-integrations-gevent.yml
index 0d57e14224..525140dfa7 100644
--- a/.github/workflows/test-integrations-gevent.yml
+++ b/.github/workflows/test-integrations-gevent.yml
@@ -17,6 +17,9 @@ concurrency:
   cancel-in-progress: true
 permissions:
   contents: read
+  actions: read
+  pull-requests: write
+  statuses: write
 env:
   BUILD_CACHE_KEY: ${{ github.sha }}
   CACHED_BUILD_PATHS: |
@@ -38,7 +41,7 @@ jobs:
     # Use Docker container only for Python 3.6
     container: ${{ matrix.python-version == '3.6' && 'python:3.6' || null }}
     steps:
-      - uses: actions/checkout@v6.0.1
+      - uses: actions/checkout@v6.0.2
       - uses: actions/setup-python@v6
         if: ${{ matrix.python-version != '3.6' }}
         with:
@@ -65,21 +68,13 @@ jobs:
         run: |
           coverage combine .coverage-sentry-*
           coverage xml
-      - name: Upload coverage to Codecov
+      - name: Parse and Upload Coverage
         if: ${{ !cancelled() }}
-        uses: codecov/codecov-action@v5.5.2
+        uses: getsentry/codecov-action@main
         with:
-          token: ${{ secrets.CODECOV_TOKEN }}
+          token: ${{ secrets.GITHUB_TOKEN }}
           files: coverage.xml
-          # make sure no plugins alter our coverage reports
-          plugins: noop
-          verbose: true
-      - name: Upload test results to Codecov
-        if: ${{ !cancelled() }}
-        uses: codecov/test-results-action@v1
-        with:
-          token: ${{ secrets.CODECOV_TOKEN }}
-          files: .junitxml
+          junit-xml-pattern: .junitxml
           verbose: true
   check_required_tests:
     name: All Gevent tests passed
diff --git a/.github/workflows/test-integrations-graphql.yml b/.github/workflows/test-integrations-graphql.yml
index 8e27210148..322a95ff54 100644
--- a/.github/workflows/test-integrations-graphql.yml
+++ b/.github/workflows/test-integrations-graphql.yml
@@ -17,6 +17,9 @@ concurrency:
   cancel-in-progress: true
 permissions:
   contents: read
+  actions: read
+  pull-requests: write
+  statuses: write
 env:
   BUILD_CACHE_KEY: ${{ github.sha }}
   CACHED_BUILD_PATHS: |
@@ -38,7 +41,7 @@ jobs:
     # Use Docker container only for Python 3.6
     container: ${{ matrix.python-version == '3.6' && 'python:3.6' || null }}
     steps:
-      - uses: actions/checkout@v6.0.1
+      - uses: actions/checkout@v6.0.2
       - uses: actions/setup-python@v6
         if: ${{ matrix.python-version != '3.6' }}
         with:
@@ -77,21 +80,13 @@ jobs:
         run: |
           coverage combine .coverage-sentry-*
           coverage xml
-      - name: Upload coverage to Codecov
+      - name: Parse and Upload Coverage
         if: ${{ !cancelled() }}
-        uses: codecov/codecov-action@v5.5.2
+        uses: getsentry/codecov-action@main
         with:
-          token: ${{ secrets.CODECOV_TOKEN }}
+          token: ${{ secrets.GITHUB_TOKEN }}
           files: coverage.xml
-          # make sure no plugins alter our coverage reports
-          plugins: noop
-          verbose: true
-      - name: Upload test results to Codecov
-        if: ${{ !cancelled() }}
-        uses: codecov/test-results-action@v1
-        with:
-          token: ${{ secrets.CODECOV_TOKEN }}
-          files: .junitxml
+          junit-xml-pattern: .junitxml
           verbose: true
   check_required_tests:
     name: All GraphQL tests passed
diff --git a/.github/workflows/test-integrations-mcp.yml b/.github/workflows/test-integrations-mcp.yml
index e986d1e358..4b576a897f 100644
--- a/.github/workflows/test-integrations-mcp.yml
+++ b/.github/workflows/test-integrations-mcp.yml
@@ -17,6 +17,9 @@ concurrency:
   cancel-in-progress: true
 permissions:
   contents: read
+  actions: read
+  pull-requests: write
+  statuses: write
 env:
   BUILD_CACHE_KEY: ${{ github.sha }}
   CACHED_BUILD_PATHS: |
@@ -38,7 +41,7 @@ jobs:
     # Use Docker container only for Python 3.6
     container: ${{ matrix.python-version == '3.6' && 'python:3.6' || null }}
     steps:
-      - uses: actions/checkout@v6.0.1
+      - uses: actions/checkout@v6.0.2
       - uses: actions/setup-python@v6
         if: ${{ matrix.python-version != '3.6' }}
         with:
@@ -69,21 +72,13 @@ jobs:
         run: |
           coverage combine .coverage-sentry-*
           coverage xml
-      - name: Upload coverage to Codecov
+      - name: Parse and Upload Coverage
         if: ${{ !cancelled() }}
-        uses: codecov/codecov-action@v5.5.2
+        uses: getsentry/codecov-action@main
         with:
-          token: ${{ secrets.CODECOV_TOKEN }}
+          token: ${{ secrets.GITHUB_TOKEN }}
           files: coverage.xml
-          # make sure no plugins alter our coverage reports
-          plugins: noop
-          verbose: true
-      - name: Upload test results to Codecov
-        if: ${{ !cancelled() }}
-        uses: codecov/test-results-action@v1
-        with:
-          token: ${{ secrets.CODECOV_TOKEN }}
-          files: .junitxml
+          junit-xml-pattern: .junitxml
           verbose: true
   check_required_tests:
     name: All MCP tests passed
diff --git a/.github/workflows/test-integrations-misc.yml b/.github/workflows/test-integrations-misc.yml
index 16d8a5f1a9..021d6cda79 100644
--- a/.github/workflows/test-integrations-misc.yml
+++ b/.github/workflows/test-integrations-misc.yml
@@ -17,6 +17,9 @@ concurrency:
   cancel-in-progress: true
 permissions:
   contents: read
+  actions: read
+  pull-requests: write
+  statuses: write
 env:
   BUILD_CACHE_KEY: ${{ github.sha }}
   CACHED_BUILD_PATHS: |
@@ -38,7 +41,7 @@ jobs:
     # Use Docker container only for Python 3.6
     container: ${{ matrix.python-version == '3.6' && 'python:3.6' || null }}
     steps:
-      - uses: actions/checkout@v6.0.1
+      - uses: actions/checkout@v6.0.2
       - uses: actions/setup-python@v6
         if: ${{ matrix.python-version != '3.6' }}
         with:
@@ -97,21 +100,13 @@ jobs:
         run: |
           coverage combine .coverage-sentry-*
           coverage xml
-      - name: Upload coverage to Codecov
+      - name: Parse and Upload Coverage
         if: ${{ !cancelled() }}
-        uses: codecov/codecov-action@v5.5.2
+        uses: getsentry/codecov-action@main
         with:
-          token: ${{ secrets.CODECOV_TOKEN }}
+          token: ${{ secrets.GITHUB_TOKEN }}
           files: coverage.xml
-          # make sure no plugins alter our coverage reports
-          plugins: noop
-          verbose: true
-      - name: Upload test results to Codecov
-        if: ${{ !cancelled() }}
-        uses: codecov/test-results-action@v1
-        with:
-          token: ${{ secrets.CODECOV_TOKEN }}
-          files: .junitxml
+          junit-xml-pattern: .junitxml
           verbose: true
   check_required_tests:
     name: All Misc tests passed
diff --git a/.github/workflows/test-integrations-network.yml b/.github/workflows/test-integrations-network.yml
index af0ed3cd09..ee4579f50f 100644
--- a/.github/workflows/test-integrations-network.yml
+++ b/.github/workflows/test-integrations-network.yml
@@ -17,6 +17,9 @@ concurrency:
   cancel-in-progress: true
 permissions:
   contents: read
+  actions: read
+  pull-requests: write
+  statuses: write
 env:
   BUILD_CACHE_KEY: ${{ github.sha }}
   CACHED_BUILD_PATHS: |
@@ -38,7 +41,7 @@ jobs:
     # Use Docker container only for Python 3.6
     container: ${{ matrix.python-version == '3.6' && 'python:3.6' || null }}
     steps:
-      - uses: actions/checkout@v6.0.1
+      - uses: actions/checkout@v6.0.2
       - uses: actions/setup-python@v6
         if: ${{ matrix.python-version != '3.6' }}
         with:
@@ -73,21 +76,13 @@ jobs:
         run: |
           coverage combine .coverage-sentry-*
           coverage xml
-      - name: Upload coverage to Codecov
+      - name: Parse and Upload Coverage
         if: ${{ !cancelled() }}
-        uses: codecov/codecov-action@v5.5.2
+        uses: getsentry/codecov-action@main
         with:
-          token: ${{ secrets.CODECOV_TOKEN }}
+          token: ${{ secrets.GITHUB_TOKEN }}
           files: coverage.xml
-          # make sure no plugins alter our coverage reports
-          plugins: noop
-          verbose: true
-      - name: Upload test results to Codecov
-        if: ${{ !cancelled() }}
-        uses: codecov/test-results-action@v1
-        with:
-          token: ${{ secrets.CODECOV_TOKEN }}
-          files: .junitxml
+          junit-xml-pattern: .junitxml
           verbose: true
   check_required_tests:
     name: All Network tests passed
diff --git a/.github/workflows/test-integrations-tasks.yml b/.github/workflows/test-integrations-tasks.yml
index bf464d8f5c..bab5ddf335 100644
--- a/.github/workflows/test-integrations-tasks.yml
+++ b/.github/workflows/test-integrations-tasks.yml
@@ -17,6 +17,9 @@ concurrency:
   cancel-in-progress: true
 permissions:
   contents: read
+  actions: read
+  pull-requests: write
+  statuses: write
 env:
   BUILD_CACHE_KEY: ${{ github.sha }}
   CACHED_BUILD_PATHS: |
@@ -38,7 +41,7 @@ jobs:
     # Use Docker container only for Python 3.6
     container: ${{ matrix.python-version == '3.6' && 'python:3.6' || null }}
     steps:
-      - uses: actions/checkout@v6.0.1
+      - uses: actions/checkout@v6.0.2
       - uses: actions/setup-python@v6
         if: ${{ matrix.python-version != '3.6' }}
         with:
@@ -100,21 +103,13 @@ jobs:
         run: |
           coverage combine .coverage-sentry-*
           coverage xml
-      - name: Upload coverage to Codecov
+      - name: Parse and Upload Coverage
         if: ${{ !cancelled() }}
-        uses: codecov/codecov-action@v5.5.2
+        uses: getsentry/codecov-action@main
         with:
-          token: ${{ secrets.CODECOV_TOKEN }}
+          token: ${{ secrets.GITHUB_TOKEN }}
           files: coverage.xml
-          # make sure no plugins alter our coverage reports
-          plugins: noop
-          verbose: true
-      - name: Upload test results to Codecov
-        if: ${{ !cancelled() }}
-        uses: codecov/test-results-action@v1
-        with:
-          token: ${{ secrets.CODECOV_TOKEN }}
-          files: .junitxml
+          junit-xml-pattern: .junitxml
           verbose: true
   check_required_tests:
     name: All Tasks tests passed
diff --git a/.github/workflows/test-integrations-web-1.yml b/.github/workflows/test-integrations-web-1.yml
index 7f4c3d681f..82632632e7 100644
--- a/.github/workflows/test-integrations-web-1.yml
+++ b/.github/workflows/test-integrations-web-1.yml
@@ -17,6 +17,9 @@ concurrency:
   cancel-in-progress: true
 permissions:
   contents: read
+  actions: read
+  pull-requests: write
+  statuses: write
 env:
   BUILD_CACHE_KEY: ${{ github.sha }}
   CACHED_BUILD_PATHS: |
@@ -56,7 +59,7 @@ jobs:
     # Use Docker container only for Python 3.6
     container: ${{ matrix.python-version == '3.6' && 'python:3.6' || null }}
     steps:
-      - uses: actions/checkout@v6.0.1
+      - uses: actions/checkout@v6.0.2
       - uses: actions/setup-python@v6
         if: ${{ matrix.python-version != '3.6' }}
         with:
@@ -95,21 +98,13 @@ jobs:
         run: |
           coverage combine .coverage-sentry-*
           coverage xml
-      - name: Upload coverage to Codecov
+      - name: Parse and Upload Coverage
         if: ${{ !cancelled() }}
-        uses: codecov/codecov-action@v5.5.2
+        uses: getsentry/codecov-action@main
         with:
-          token: ${{ secrets.CODECOV_TOKEN }}
+          token: ${{ secrets.GITHUB_TOKEN }}
           files: coverage.xml
-          # make sure no plugins alter our coverage reports
-          plugins: noop
-          verbose: true
-      - name: Upload test results to Codecov
-        if: ${{ !cancelled() }}
-        uses: codecov/test-results-action@v1
-        with:
-          token: ${{ secrets.CODECOV_TOKEN }}
-          files: .junitxml
+          junit-xml-pattern: .junitxml
           verbose: true
   check_required_tests:
     name: All Web 1 tests passed
diff --git a/.github/workflows/test-integrations-web-2.yml b/.github/workflows/test-integrations-web-2.yml
index 7de840df55..9dec6bff24 100644
--- a/.github/workflows/test-integrations-web-2.yml
+++ b/.github/workflows/test-integrations-web-2.yml
@@ -17,6 +17,9 @@ concurrency:
   cancel-in-progress: true
 permissions:
   contents: read
+  actions: read
+  pull-requests: write
+  statuses: write
 env:
   BUILD_CACHE_KEY: ${{ github.sha }}
   CACHED_BUILD_PATHS: |
@@ -38,7 +41,7 @@ jobs:
     # Use Docker container only for Python 3.6
     container: ${{ matrix.python-version == '3.6' && 'python:3.6' || null }}
     steps:
-      - uses: actions/checkout@v6.0.1
+      - uses: actions/checkout@v6.0.2
       - uses: actions/setup-python@v6
         if: ${{ matrix.python-version != '3.6' }}
         with:
@@ -101,21 +104,13 @@ jobs:
         run: |
           coverage combine .coverage-sentry-*
           coverage xml
-      - name: Upload coverage to Codecov
+      - name: Parse and Upload Coverage
         if: ${{ !cancelled() }}
-        uses: codecov/codecov-action@v5.5.2
+        uses: getsentry/codecov-action@main
         with:
-          token: ${{ secrets.CODECOV_TOKEN }}
+          token: ${{ secrets.GITHUB_TOKEN }}
           files: coverage.xml
-          # make sure no plugins alter our coverage reports
-          plugins: noop
-          verbose: true
-      - name: Upload test results to Codecov
-        if: ${{ !cancelled() }}
-        uses: codecov/test-results-action@v1
-        with:
-          token: ${{ secrets.CODECOV_TOKEN }}
-          files: .junitxml
+          junit-xml-pattern: .junitxml
           verbose: true
   check_required_tests:
     name: All Web 2 tests passed
diff --git a/.github/workflows/update-tox.yml b/.github/workflows/update-tox.yml
index 5d3931cf9e..914109eae8 100644
--- a/.github/workflows/update-tox.yml
+++ b/.github/workflows/update-tox.yml
@@ -23,7 +23,7 @@ jobs:
           python-version: 3.14t
 
       - name: Checkout repo
-        uses: actions/checkout@v6.0.1
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
         with:
           token: ${{ secrets.GITHUB_TOKEN }}
 
diff --git a/CHANGELOG.md b/CHANGELOG.md
index 8592487cb8..7840cfa595 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -1,5 +1,167 @@
 # Changelog
 
+## 2.51.0
+
+### New Features ✨
+
+#### Openai
+
+- feat(openai): Set system instruction attribute for Responses API by @alexander-alderman-webb in [#5376](https://github.com/getsentry/sentry-python/pull/5376)
+- feat(openai): Set system instruction attribute for Completions API by @alexander-alderman-webb in [#5358](https://github.com/getsentry/sentry-python/pull/5358)
+- feat(integrations): OpenAI/OpenAI Agents detect and report the time to first token metric (TTFT) as `gen_ai.response.time_to_first_token` by @constantinius in [#5348](https://github.com/getsentry/sentry-python/pull/5348)
+
+#### Openai Agents
+
+- feat(openai-agents): Set system instruction attribute on `gen_ai.chat` spans by @alexander-alderman-webb in [#5370](https://github.com/getsentry/sentry-python/pull/5370)
+- feat(openai-agents): Set system instruction attribute by @alexander-alderman-webb in [#5355](https://github.com/getsentry/sentry-python/pull/5355)
+- feat(integrations): openai-agents streaming support by @constantinius in [#5291](https://github.com/getsentry/sentry-python/pull/5291)
+
+#### Other
+
+- feat(ai): Add original input length meta attribute by @alexander-alderman-webb in [#5375](https://github.com/getsentry/sentry-python/pull/5375)
+- feat(anthropic): Set system instruction attribute by @alexander-alderman-webb in [#5353](https://github.com/getsentry/sentry-python/pull/5353)
+- feat(asyncio): Allow to turn task spans off by @sentrivana in [#5367](https://github.com/getsentry/sentry-python/pull/5367)
+- feat(gen_ai): add function `set_conversation_id` and managing functions on the Scope and apply it on the Span on `.finish()` by @constantinius in [#5362](https://github.com/getsentry/sentry-python/pull/5362)
+- feat(google-genai): Set system instruction attribute by @alexander-alderman-webb in [#5354](https://github.com/getsentry/sentry-python/pull/5354)
+- feat(langchain): Set system instruction attribute by @alexander-alderman-webb in [#5357](https://github.com/getsentry/sentry-python/pull/5357)
+- feat(pydantic-ai): Set system instruction attribute by @alexander-alderman-webb in [#5356](https://github.com/getsentry/sentry-python/pull/5356)
+- feat(transport): Report 413 responses for oversized envelopes by @alexander-alderman-webb in [#5380](https://github.com/getsentry/sentry-python/pull/5380)
+
+### Bug Fixes 🐛
+
+- fix(ai): Keep single content input message by @alexander-alderman-webb in [#5345](https://github.com/getsentry/sentry-python/pull/5345)
+
+### Internal Changes 🔧
+
+- ci(release): Fix changelog-preview permissions by @BYK in [#5368](https://github.com/getsentry/sentry-python/pull/5368)
+- ref: Replace `set_data_normalized()` with `Span.set_data()` for system instructions by @alexander-alderman-webb in [#5374](https://github.com/getsentry/sentry-python/pull/5374)
+- ci: Fix path in AI integration tests by @alexander-alderman-webb in [#5347](https://github.com/getsentry/sentry-python/pull/5347)
+
+## 2.50.0
+
+### New Features ✨
+
+#### Ai
+
+- feat(ai): add cache writes for gen_ai by @shellmayr in [#5319](https://github.com/getsentry/sentry-python/pull/5319)
+- feat(ai): add parse_data_uri function to parse a data URI by @constantinius in [#5311](https://github.com/getsentry/sentry-python/pull/5311)
+
+#### Other
+
+- feat(asyncio): Add on-demand way to enable AsyncioIntegration by @sentrivana in [#5288](https://github.com/getsentry/sentry-python/pull/5288)
+
+  You can now enable the `AsyncioIntegration` on demand, after calling `sentry_sdk.init()`. This is useful in scenarios where you don't have
+  the event loop running early on, or when you need to instrument multiple event loops.
+
+```python
+import sentry_sdk
+from sentry_sdk.integrations.asyncio import enable_asyncio_integration
+
+# Initializing the SDK as early as possible, when there is no event loop yet
+sentry_sdk.init(
+    ...
+    # No AsyncioIntegration in explicitly provided `integrations`
+)
+
+async def main():
+    enable_asyncio_integration()  # instruments the current event loop
+    # ...your code...
+```
+
+- feat(openai-agents): Inject propagation headers for `HostedMCPTool` by @alexander-alderman-webb in [#5297](https://github.com/getsentry/sentry-python/pull/5297)
+- feat(stdlib): Handle proxy tunnels in httlib integration by @sl0thentr0py in [#5303](https://github.com/getsentry/sentry-python/pull/5303)
+- feat: Support array types for logs and metrics attributes by @alexander-alderman-webb in [#5314](https://github.com/getsentry/sentry-python/pull/5314)
+
+### Bug Fixes 🐛
+
+#### Integrations
+
+- fix(integrations): google genai report image inputs by @constantinius in [#5337](https://github.com/getsentry/sentry-python/pull/5337)
+- fix(integrations): google-genai: reworked `gen_ai.request.messages` extraction from parameters by @constantinius in [#5275](https://github.com/getsentry/sentry-python/pull/5275)
+- fix(integrations): pydantic-ai: properly format binary input message parts to be conformant with the `gen_ai.request.messages` structure by @constantinius in [#5251](https://github.com/getsentry/sentry-python/pull/5251)
+- fix(integrations): Anthropic: add content transformation for images and documents by @constantinius in [#5276](https://github.com/getsentry/sentry-python/pull/5276)
+- fix(integrations): langchain add multimodal content transformation functions for images, audio, and files by @constantinius in [#5278](https://github.com/getsentry/sentry-python/pull/5278)
+
+#### Litellm
+
+- fix(litellm): fix `gen_ai.request.messages` to be as expected by @constantinius in [#5255](https://github.com/getsentry/sentry-python/pull/5255)
+- fix(litellm): Guard against module shadowing by @alexander-alderman-webb in [#5249](https://github.com/getsentry/sentry-python/pull/5249)
+
+#### Other
+
+- fix(ai): redact message parts content of type blob by @constantinius in [#5243](https://github.com/getsentry/sentry-python/pull/5243)
+- fix(clickhouse): Guard against module shadowing by @alexander-alderman-webb in [#5250](https://github.com/getsentry/sentry-python/pull/5250)
+- fix(gql): Revert signature change of patched gql.Client.execute by @alexander-alderman-webb in [#5289](https://github.com/getsentry/sentry-python/pull/5289)
+- fix(grpc): Derive interception state from channel fields by @alexander-alderman-webb in [#5302](https://github.com/getsentry/sentry-python/pull/5302)
+- fix(pure-eval): Guard against module shadowing by @alexander-alderman-webb in [#5252](https://github.com/getsentry/sentry-python/pull/5252)
+- fix(ray): Guard against module shadowing by @alexander-alderman-webb in [#5254](https://github.com/getsentry/sentry-python/pull/5254)
+- fix(threading): Handle channels shadowing by @sentrivana in [#5299](https://github.com/getsentry/sentry-python/pull/5299)
+- fix(typer): Guard against module shadowing by @alexander-alderman-webb in [#5253](https://github.com/getsentry/sentry-python/pull/5253)
+- fix: Stop suppressing exception chains in AI integrations by @alexander-alderman-webb in [#5309](https://github.com/getsentry/sentry-python/pull/5309)
+- fix: Send client reports for span recorder overflow by @sentrivana in [#5310](https://github.com/getsentry/sentry-python/pull/5310)
+
+### Documentation 📚
+
+- docs(metrics): Remove experimental notice by @alexander-alderman-webb in [#5304](https://github.com/getsentry/sentry-python/pull/5304)
+- docs: Update Python versions banner in README by @sentrivana in [#5287](https://github.com/getsentry/sentry-python/pull/5287)
+
+### Internal Changes 🔧
+
+#### Fastmcp
+
+- test(fastmcp): Narrow `AttributeError` try-except by @alexander-alderman-webb in [#5339](https://github.com/getsentry/sentry-python/pull/5339)
+- test(fastmcp): Stop accessing non-existent attribute by @alexander-alderman-webb in [#5338](https://github.com/getsentry/sentry-python/pull/5338)
+
+#### Release
+
+- ci(release): Bump Craft version to fix issues by @BYK in [#5305](https://github.com/getsentry/sentry-python/pull/5305)
+- ci(release): Switch from action-prepare-release to Craft by @BYK in [#5290](https://github.com/getsentry/sentry-python/pull/5290)
+
+#### Other
+
+- chore(gen_ai): add auto-enablement for google genai by @shellmayr in [#5295](https://github.com/getsentry/sentry-python/pull/5295)
+- chore(repo): Add Claude Code settings with basic permissions by @philipphofmann in [#5342](https://github.com/getsentry/sentry-python/pull/5342)
+- ci: 🤖 Update test matrix with new releases (01/19) by @github-actions in [#5330](https://github.com/getsentry/sentry-python/pull/5330)
+- ci: Add periodic AI integration tests by @alexander-alderman-webb in [#5313](https://github.com/getsentry/sentry-python/pull/5313)
+- chore: Use pull_request_target for changelog preview by @BYK in [#5323](https://github.com/getsentry/sentry-python/pull/5323)
+- chore: add unlabeled trigger to changelog-preview by @BYK in [#5315](https://github.com/getsentry/sentry-python/pull/5315)
+- chore: Add type for metric units by @sentrivana in [#5312](https://github.com/getsentry/sentry-python/pull/5312)
+- ci: Update tox and handle generic classifiers by @sentrivana in [#5306](https://github.com/getsentry/sentry-python/pull/5306)
+
+## 2.49.0
+
+### New Features ✨
+
+- feat(api): Add `Scope.set_attribute` by @sentrivana in [#5256](https://github.com/getsentry/sentry-python/pull/5256)
+
+### Bug Fixes 🐛
+
+- fix(grpc): Gate third-party imports by @alexander-alderman-webb in [#5246](https://github.com/getsentry/sentry-python/pull/5246)
+- fix(opentelemetry): Gate third-party imports by @alexander-alderman-webb in [#5247](https://github.com/getsentry/sentry-python/pull/5247)
+- fix(ray): Keep variadic kwargs last in signatures by @alexander-alderman-webb in [#5244](https://github.com/getsentry/sentry-python/pull/5244)
+- fix(trytond): Gate third-party imports by @alexander-alderman-webb in [#5245](https://github.com/getsentry/sentry-python/pull/5245)
+- Fix openai count_tokens by @sl0thentr0py in [#5281](https://github.com/getsentry/sentry-python/pull/5281)
+
+### Documentation 📚
+
+- docs: Fix typo in comment by @sentrivana in [#5280](https://github.com/getsentry/sentry-python/pull/5280)
+- docs: Fix `middleware_spans` docstring by @sentrivana in [#5279](https://github.com/getsentry/sentry-python/pull/5279)
+
+### Internal Changes 🔧
+
+- ref(scope): Set global attrs on global scope by @sentrivana in [#5259](https://github.com/getsentry/sentry-python/pull/5259)
+- chore: Ignore type migration for scripts/ and tests/ in blame by @alexander-alderman-webb in [#5284](https://github.com/getsentry/sentry-python/pull/5284)
+- ref: Properly override parent func by @sentrivana in [#5283](https://github.com/getsentry/sentry-python/pull/5283)
+- ci: Allow to use Craft's new auto-versioning by @sentrivana in [#5218](https://github.com/getsentry/sentry-python/pull/5218)
+- ref: Deduplicate batchers by @sentrivana in [#5263](https://github.com/getsentry/sentry-python/pull/5263)
+- tests: Add dedicated transport format test for metrics, logs by @sentrivana in [#5264](https://github.com/getsentry/sentry-python/pull/5264)
+- ci: 🤖 Update test matrix with new releases (01/05) by @github-actions in [#5273](https://github.com/getsentry/sentry-python/pull/5273)
+- tests: General logs tests should use Sentry logs API by @sentrivana in [#5262](https://github.com/getsentry/sentry-python/pull/5262)
+- tests: Test preserialization of attributes by @sentrivana in [#5260](https://github.com/getsentry/sentry-python/pull/5260)
+- ci: Unpin Pydantic 1.x version in tests by @alexander-alderman-webb in [#5261](https://github.com/getsentry/sentry-python/pull/5261)
+- ref: Make logs, metrics go via scope by @sentrivana in [#5213](https://github.com/getsentry/sentry-python/pull/5213)
+- ci: Fix failing arq, fastapi tests on 3.7; update test matrix by @sentrivana in [#5258](https://github.com/getsentry/sentry-python/pull/5258)
+
 ## 2.48.0
 
 Middleware spans are now disabled by default in Django, Starlette and FastAPI integrations. Set the `middleware_spans` integration-level
diff --git a/README.md b/README.md
index 6c1db3b25f..7a7bf8b44f 100644
--- a/README.md
+++ b/README.md
@@ -9,7 +9,7 @@ _Bad software is everywhere, and we're tired of it. Sentry is on a mission to he
 [![Discord](https://img.shields.io/discord/621778831602221064?logo=discord&labelColor=%20%235462eb&logoColor=%20%23f5f5f5&color=%20%235462eb)](https://discord.com/invite/Ww9hbqr)
 [![X Follow](https://img.shields.io/twitter/follow/sentry?label=sentry&style=social)](https://x.com/intent/follow?screen_name=sentry)
 [![PyPi page link -- version](https://img.shields.io/pypi/v/sentry-sdk.svg)](https://pypi.python.org/pypi/sentry-sdk)
-<img src="https://img.shields.io/badge/python-3.7 | 3.8 | 3.9 | 3.10 | 3.11 | 3.12 | 3.13-blue.svg" alt="python">
+<img src="https://img.shields.io/badge/python-3.7 | 3.8 | 3.9 | 3.10 | 3.11 | 3.12 | 3.13 | 3.14-blue.svg" alt="python">
 [![Build Status](https://github.com/getsentry/sentry-python/actions/workflows/ci.yml/badge.svg)](https://github.com/getsentry/sentry-python/actions/workflows/ci.yml)
 
 <br/>
diff --git a/codecov.yml b/codecov.yml
index b7abcf8c86..4cb22edee8 100644
--- a/codecov.yml
+++ b/codecov.yml
@@ -10,18 +10,7 @@ ignore:
   - "tests"
   - "sentry_sdk/_types.py"
 
-# Read more here: https://docs.codecov.com/docs/pull-request-comments
-comment:
-  after_n_builds: 99
-  layout: 'diff, files'
-  # Update, if comment exists. Otherwise post new.
-  behavior: default
-  # Comments will only post when coverage changes. Furthermore, if a comment
-  # already exists, and a newer commit results in no coverage change for the
-  # entire pull, the comment will be deleted.
-  require_changes: true
-  require_base: true  # must have a base report to post
-  require_head: true  # must have a head report to post
+comment: true
 
 github_checks:
   annotations: false
diff --git a/docs/conf.py b/docs/conf.py
index 4ce462103f..2049969d4c 100644
--- a/docs/conf.py
+++ b/docs/conf.py
@@ -31,7 +31,7 @@
 copyright = "2019-{}, Sentry Team and Contributors".format(datetime.now().year)
 author = "Sentry Team and Contributors"
 
-release = "2.48.0"
+release = "2.51.0"
 version = ".".join(release.split(".")[:2])  # The short X.Y version.
 
 
diff --git a/scripts/find_raise_from_none.py b/scripts/find_raise_from_none.py
new file mode 100644
index 0000000000..63b2b84333
--- /dev/null
+++ b/scripts/find_raise_from_none.py
@@ -0,0 +1,65 @@
+import ast
+import pathlib
+from collections import defaultdict
+
+
+class RaiseFromNoneVisitor(ast.NodeVisitor):
+    line_numbers = defaultdict(list)
+
+    def __init__(self, filename):
+        self.filename = filename
+
+    def visit_Raise(self, node: ast.Raise):
+        if node.cause is not None:
+            if isinstance(node.cause, ast.Constant) and node.cause.value is None:
+                RaiseFromNoneVisitor.line_numbers[self.filename].append(node.lineno)
+        self.generic_visit(node)
+
+
+def scan_file(module_path: pathlib.Path):
+    source = pathlib.Path(module_path).read_text(encoding="utf-8")
+    tree = ast.parse(source, filename=module_path)
+
+    RaiseFromNoneVisitor(module_path).visit(tree)
+
+
+def walk_package_modules():
+    for p in pathlib.Path("sentry_sdk").rglob("*.py"):
+        yield p
+
+
+def format_detected_raises(line_numbers) -> str:
+    lines = []
+    for filepath, line_numbers_in_file in line_numbers.items():
+        lines_string = ", ".join(f"line {ln}" for ln in sorted(line_numbers_in_file))
+        lines.append(
+            f"{filepath}: {len(line_numbers_in_file)} occurrence(s) at {lines_string}"
+        )
+    return "\n".join(lines)
+
+
+def main():
+    for module_path in walk_package_modules():
+        scan_file(module_path)
+
+    # TODO: Investigate why we suppress exception chains here.
+    ignored_raises = {
+        pathlib.Path("sentry_sdk/integrations/asgi.py"): 2,
+        pathlib.Path("sentry_sdk/integrations/asyncio.py"): 1,
+    }
+
+    raise_from_none_count = {
+        file: len(occurences)
+        for file, occurences in RaiseFromNoneVisitor.line_numbers.items()
+    }
+    if raise_from_none_count != ignored_raises:
+        exc = Exception("Detected unexpected raise ... from None.")
+        exc.add_note(
+            "Raise ... from None suppresses chained exceptions, removing valuable context."
+        )
+        exc.add_note(format_detected_raises(RaiseFromNoneVisitor.line_numbers))
+        raise exc
+
+
+if __name__ == "__main__":
+    main()
diff --git a/scripts/populate_tox/config.py b/scripts/populate_tox/config.py
index 9d5e97846b..37d3a6a64d 100644
--- a/scripts/populate_tox/config.py
+++ b/scripts/populate_tox/config.py
@@ -311,6 +311,9 @@
         "deps": {
             "*": ["mockupdb"],
         },
+        "python": {
+            "<3.6": "<3.7",
+        },
     },
     "pyramid": {
         "package": "pyramid",
@@ -368,6 +371,9 @@
             ">=0.9,<0.14": ["fakeredis>=1.0,<1.7.4"],
             "py3.6,py3.7": ["fakeredis!=2.26.0"],
         },
+        "python": {
+            "<0.13": "<3.7",
+        },
     },
     "sanic": {
         "package": "sanic",
@@ -385,6 +391,9 @@
     },
     "sqlalchemy": {
         "package": "sqlalchemy",
+        "python": {
+            "<1.4": "<3.10",
+        },
     },
     "starlette": {
         "package": "starlette",
diff --git a/scripts/populate_tox/package_dependencies.jsonl b/scripts/populate_tox/package_dependencies.jsonl
index 3c32b3cb93..52724708f4 100644
--- a/scripts/populate_tox/package_dependencies.jsonl
+++ b/scripts/populate_tox/package_dependencies.jsonl
@@ -1,29 +1,35 @@
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diff --git a/scripts/populate_tox/populate_tox.py b/scripts/populate_tox/populate_tox.py
index ce0983ad50..196a4d76fe 100644
--- a/scripts/populate_tox/populate_tox.py
+++ b/scripts/populate_tox/populate_tox.py
@@ -77,6 +77,14 @@
 MIN_FREE_THREADING_SUPPORT = Version("3.14")
 
 
+class PackageVersion(Version):
+    # Convenience wrapper around Version. It's convenient to be able to set
+    # attributes on a Version in toxgen, but we can't because the class now
+    # defines __slots__. By rewrapping Version in this custom class, we get
+    # around that.
+    pass
+
+
 @dataclass(order=True)
 class ThreadedVersion:
     version: Version
@@ -218,7 +226,7 @@ def _save_to_package_dependencies_cache(
 def _prefilter_releases(
     integration: str,
     releases: dict[str, dict],
-) -> tuple[list[Version], Optional[Version]]:
+) -> tuple[list[PackageVersion], Optional[PackageVersion]]:
     """
     Filter `releases`, removing releases that are for sure unsupported.
 
@@ -238,7 +246,7 @@ def _prefilter_releases(
 
     min_supported = _MIN_VERSIONS.get(integration_name)
     if min_supported is not None:
-        min_supported = Version(".".join(map(str, min_supported)))
+        min_supported = PackageVersion(".".join(map(str, min_supported)))
     else:
         print(
             f"  {integration} doesn't have a minimum version defined in "
@@ -291,10 +299,10 @@ def _prefilter_releases(
             ):
                 # Don't save all patch versions of a release, just the newest one
                 if version.micro > saved_version.micro:
-                    filtered_releases[i] = version
+                    filtered_releases[i] = PackageVersion(str(version))
                 break
         else:
-            filtered_releases.append(version)
+            filtered_releases.append(PackageVersion(str(version)))
 
     filtered_releases.sort()
 
@@ -302,14 +310,14 @@ def _prefilter_releases(
     # than the last released version); if not, don't consider it
     if last_prerelease is not None:
         if not filtered_releases or last_prerelease > filtered_releases[-1]:
-            return filtered_releases, last_prerelease
+            return filtered_releases, PackageVersion(str(last_prerelease))
 
     return filtered_releases, None
 
 
 def get_supported_releases(
     integration: str, pypi_data: dict
-) -> tuple[list[Version], Optional[Version]]:
+) -> tuple[list[PackageVersion], Optional[PackageVersion]]:
     """
     Get a list of releases that are currently supported by the SDK.
 
@@ -331,7 +339,7 @@ def get_supported_releases(
         pypi_data["releases"],
     )
 
-    def _supports_lowest(release: Version) -> bool:
+    def _supports_lowest(release: PackageVersion) -> bool:
         time.sleep(PYPI_COOLDOWN)  # don't DoS PYPI
 
         pypi_data = fetch_release(package, release)
@@ -504,6 +512,9 @@ def pick_python_versions_to_test(
     - a free-threaded wheel is distributed; and
     - the SDK supports free-threading.
     """
+    if not python_versions:
+        return []
+
     filtered_python_versions = {
         python_versions[0],
     }
@@ -545,7 +556,8 @@ def _parse_python_versions_from_classifiers(classifiers: list[str]) -> list[Vers
 
     if python_versions:
         python_versions.sort()
-        return python_versions
+
+    return python_versions
 
 
 def determine_python_versions(pypi_data: dict) -> Union[SpecifierSet, list[Version]]:
@@ -579,6 +591,14 @@ def determine_python_versions(pypi_data: dict) -> Union[SpecifierSet, list[Versi
     if requires_python:
         return SpecifierSet(requires_python)
 
+    # If we haven't found neither specific 3.x classifiers nor a requires_python,
+    # check if there is a generic "Python 3" classifier and if so, assume the
+    # package supports all Python versions the SDK does. If this is not the case
+    # in reality, add the actual constraints manually to config.py.
+    for classifier in classifiers:
+        if CLASSIFIER_PREFIX + "3" in classifiers:
+            return SpecifierSet(f">={MIN_PYTHON_VERSION}")
+
     return []
 
 
@@ -770,7 +790,7 @@ def _compare_min_version_with_defined(
 
 
 def _add_python_versions_to_release(
-    integration: str, package: str, release: Version
+    integration: str, package: str, release: PackageVersion
 ) -> None:
     release_pypi_data = fetch_release(package, release)
     if release_pypi_data is None:
diff --git a/scripts/populate_tox/releases.jsonl b/scripts/populate_tox/releases.jsonl
index 3c6b99e8ff..67abdf36d2 100644
--- a/scripts/populate_tox/releases.jsonl
+++ b/scripts/populate_tox/releases.jsonl
@@ -6,39 +6,40 @@
 {"info": {"classifiers": ["Development Status :: 5 - Production/Stable", "Environment :: Web Environment", "Framework :: Django", "Intended Audience :: Developers", "License :: OSI Approved :: BSD License", "Operating System :: OS Independent", "Programming Language :: Python", "Programming Language :: Python :: 3", "Programming Language :: Python :: 3 :: Only", "Programming Language :: Python :: 3.6", "Programming Language :: Python :: 3.7", "Programming Language :: Python :: 3.8", "Programming Language :: Python :: 3.9", "Topic :: Internet :: WWW/HTTP", "Topic :: Internet :: WWW/HTTP :: Dynamic Content", "Topic :: Internet :: WWW/HTTP :: WSGI", "Topic :: Software Development :: Libraries :: Application Frameworks", "Topic :: Software Development :: Libraries :: Python Modules"], "name": "Django", "requires_python": ">=3.6", "version": "3.1.14", "yanked": false}, "urls": [{"packagetype": "bdist_wheel", "filename": "Django-3.1.14-py3-none-any.whl"}, {"packagetype": "sdist", "filename": "Django-3.1.14.tar.gz"}]}
 {"info": {"classifiers": ["Development Status :: 5 - Production/Stable", "Environment :: Web Environment", "Framework :: Django", "Intended Audience :: Developers", "License :: OSI Approved :: BSD License", "Operating System :: OS Independent", "Programming Language :: Python", "Programming Language :: Python :: 3", "Programming Language :: Python :: 3 :: Only", "Programming Language :: Python :: 3.10", "Programming Language :: Python :: 3.6", "Programming Language :: Python :: 3.7", "Programming Language :: Python :: 3.8", "Programming Language :: Python :: 3.9", "Topic :: Internet :: WWW/HTTP", "Topic :: Internet :: WWW/HTTP :: Dynamic Content", "Topic :: Internet :: WWW/HTTP :: WSGI", "Topic :: Software Development :: Libraries :: Application Frameworks", "Topic :: Software Development :: Libraries :: Python Modules"], "name": "Django", "requires_python": ">=3.6", "version": "3.2.25", "yanked": false}, "urls": [{"packagetype": "bdist_wheel", "filename": "Django-3.2.25-py3-none-any.whl"}, {"packagetype": "sdist", "filename": "Django-3.2.25.tar.gz"}]}
 {"info": {"classifiers": ["Development Status :: 5 - Production/Stable", "Environment :: Web Environment", "Framework :: Django", "Intended Audience :: Developers", "License :: OSI Approved :: BSD License", "Operating System :: OS Independent", "Programming Language :: Python", "Programming Language :: Python :: 3", "Programming Language :: Python :: 3 :: Only", "Programming Language :: Python :: 3.10", "Programming Language :: Python :: 3.11", "Programming Language :: Python :: 3.12", "Programming Language :: Python :: 3.8", "Programming Language :: Python :: 3.9", "Topic :: Internet :: WWW/HTTP", "Topic :: Internet :: WWW/HTTP :: Dynamic Content", "Topic :: Internet :: WWW/HTTP :: WSGI", "Topic :: Software Development :: Libraries :: Application Frameworks", "Topic :: Software Development :: Libraries :: Python Modules"], "name": "Django", "requires_python": ">=3.8", "version": "4.2.27", "yanked": false}, "urls": [{"packagetype": "bdist_wheel", "filename": "django-4.2.27-py3-none-any.whl"}, {"packagetype": "sdist", "filename": "django-4.2.27.tar.gz"}]}
-{"info": {"classifiers": ["Development Status :: 5 - Production/Stable", "Environment :: Web Environment", "Framework :: Django", "Intended Audience :: Developers", "Operating System :: OS Independent", "Programming Language :: Python", "Programming Language :: Python :: 3", "Programming Language :: Python :: 3 :: Only", "Programming Language :: Python :: 3.10", "Programming Language :: Python :: 3.11", "Programming Language :: Python :: 3.12", "Programming Language :: Python :: 3.13", "Programming Language :: Python :: 3.14", "Topic :: Internet :: WWW/HTTP", "Topic :: Internet :: WWW/HTTP :: Dynamic Content", "Topic :: Internet :: WWW/HTTP :: WSGI", "Topic :: Software Development :: Libraries :: Application Frameworks", "Topic :: Software Development :: Libraries :: Python Modules"], "name": "Django", "requires_python": ">=3.10", "version": "5.2.9", "yanked": false}, "urls": [{"packagetype": "bdist_wheel", "filename": "django-5.2.9-py3-none-any.whl"}, {"packagetype": "sdist", "filename": "django-5.2.9.tar.gz"}]}
-{"info": {"classifiers": ["Development Status :: 5 - Production/Stable", "Environment :: Web Environment", "Framework :: Django", "Intended Audience :: Developers", "Operating System :: OS Independent", "Programming Language :: Python", "Programming Language :: Python :: 3", "Programming Language :: Python :: 3 :: Only", "Programming Language :: Python :: 3.12", "Programming Language :: Python :: 3.13", "Programming Language :: Python :: 3.14", "Topic :: Internet :: WWW/HTTP", "Topic :: Internet :: WWW/HTTP :: Dynamic Content", "Topic :: Internet :: WWW/HTTP :: WSGI", "Topic :: Software Development :: Libraries :: Application Frameworks", "Topic :: Software Development :: Libraries :: Python Modules"], "name": "Django", "requires_python": ">=3.12", "version": "6.0", "yanked": false}, "urls": [{"packagetype": "bdist_wheel", "filename": "django-6.0-py3-none-any.whl"}, {"packagetype": "sdist", "filename": "django-6.0.tar.gz"}]}
+{"info": {"classifiers": ["Development Status :: 5 - Production/Stable", "Environment :: Web Environment", "Framework :: Django", "Intended Audience :: Developers", "Operating System :: OS Independent", "Programming Language :: Python", "Programming Language :: Python :: 3", "Programming Language :: Python :: 3 :: Only", "Programming Language :: Python :: 3.10", "Programming Language :: Python :: 3.11", "Programming Language :: Python :: 3.12", "Programming Language :: Python :: 3.13", "Programming Language :: Python :: 3.14", "Topic :: Internet :: WWW/HTTP", "Topic :: Internet :: WWW/HTTP :: Dynamic Content", "Topic :: Internet :: WWW/HTTP :: WSGI", "Topic :: Software Development :: Libraries :: Application Frameworks", "Topic :: Software Development :: Libraries :: Python Modules"], "name": "Django", "requires_python": ">=3.10", "version": "5.2.10", "yanked": false}, "urls": [{"packagetype": "bdist_wheel", "filename": "django-5.2.10-py3-none-any.whl"}, {"packagetype": "sdist", "filename": "django-5.2.10.tar.gz"}]}
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+{"info": {"classifiers": ["Development Status :: 5 - Production/Stable", "Intended Audience :: Developers", "License :: OSI Approved :: MIT License", "Topic :: Software Development :: Libraries", "Topic :: Software Development :: Libraries :: Python Modules"], "name": "strawberry-graphql", "requires_python": "<4.0,>=3.10", "version": "0.291.0", "yanked": false}, "urls": [{"packagetype": "bdist_wheel", "filename": "strawberry_graphql-0.291.0-py3-none-any.whl"}, {"packagetype": "sdist", "filename": "strawberry_graphql-0.291.0.tar.gz"}]}
 {"info": {"classifiers": ["License :: OSI Approved :: Apache Software License", "Programming Language :: Python :: 3", "Programming Language :: Python :: 3.5", "Programming Language :: Python :: 3.6", "Programming Language :: Python :: 3.7", "Programming Language :: Python :: 3.8", "Programming Language :: Python :: Implementation :: CPython", "Programming Language :: Python :: Implementation :: PyPy"], "name": "tornado", "requires_python": ">= 3.5", "version": "6.0.4", "yanked": false}, "urls": [{"packagetype": "bdist_wheel", "filename": "tornado-6.0.4-cp35-cp35m-win32.whl"}, {"packagetype": "bdist_wheel", "filename": "tornado-6.0.4-cp35-cp35m-win_amd64.whl"}, {"packagetype": "bdist_wheel", "filename": "tornado-6.0.4-cp36-cp36m-win32.whl"}, {"packagetype": "bdist_wheel", "filename": "tornado-6.0.4-cp36-cp36m-win_amd64.whl"}, {"packagetype": "bdist_wheel", "filename": "tornado-6.0.4-cp37-cp37m-win32.whl"}, {"packagetype": "bdist_wheel", "filename": "tornado-6.0.4-cp37-cp37m-win_amd64.whl"}, {"packagetype": "bdist_wheel", "filename": "tornado-6.0.4-cp38-cp38-win32.whl"}, {"packagetype": "bdist_wheel", "filename": "tornado-6.0.4-cp38-cp38-win_amd64.whl"}, {"packagetype": "sdist", "filename": "tornado-6.0.4.tar.gz"}]}
 {"info": {"classifiers": ["License :: OSI Approved :: Apache Software License", "Programming Language :: Python :: 3", "Programming Language :: Python :: 3.10", "Programming Language :: Python :: 3.11", "Programming Language :: Python :: 3.12", "Programming Language :: Python :: 3.13", "Programming Language :: Python :: 3.9", "Programming Language :: Python :: Implementation :: CPython", "Programming Language :: Python :: Implementation :: PyPy"], "name": "tornado", "requires_python": ">=3.9", "version": "6.5.4", "yanked": false}, "urls": [{"packagetype": "bdist_wheel", "filename": "tornado-6.5.4-cp39-abi3-macosx_10_9_universal2.whl"}, {"packagetype": "bdist_wheel", "filename": "tornado-6.5.4-cp39-abi3-macosx_10_9_x86_64.whl"}, {"packagetype": "bdist_wheel", "filename": "tornado-6.5.4-cp39-abi3-manylinux_2_17_aarch64.manylinux2014_aarch64.whl"}, {"packagetype": "bdist_wheel", "filename": "tornado-6.5.4-cp39-abi3-manylinux_2_5_i686.manylinux1_i686.manylinux_2_17_i686.manylinux2014_i686.whl"}, {"packagetype": "bdist_wheel", "filename": "tornado-6.5.4-cp39-abi3-manylinux_2_5_x86_64.manylinux1_x86_64.manylinux_2_17_x86_64.manylinux2014_x86_64.whl"}, {"packagetype": "bdist_wheel", "filename": "tornado-6.5.4-cp39-abi3-musllinux_1_2_aarch64.whl"}, {"packagetype": "bdist_wheel", "filename": "tornado-6.5.4-cp39-abi3-musllinux_1_2_i686.whl"}, {"packagetype": "bdist_wheel", "filename": "tornado-6.5.4-cp39-abi3-musllinux_1_2_x86_64.whl"}, {"packagetype": "bdist_wheel", "filename": "tornado-6.5.4-cp39-abi3-win32.whl"}, {"packagetype": "bdist_wheel", "filename": "tornado-6.5.4-cp39-abi3-win_amd64.whl"}, {"packagetype": "bdist_wheel", "filename": "tornado-6.5.4-cp39-abi3-win_arm64.whl"}, {"packagetype": "sdist", "filename": "tornado-6.5.4.tar.gz"}]}
 {"info": {"classifiers": ["Development Status :: 5 - Production/Stable", "Environment :: No Input/Output (Daemon)", "Intended Audience :: Developers", "License :: OSI Approved :: GNU General Public License (GPL)", "Natural Language :: English", "Natural Language :: French", "Natural Language :: German", "Natural Language :: Spanish", "Operating System :: OS Independent", "Programming Language :: Python", "Topic :: Software Development :: Libraries :: Application Frameworks"], "name": "trytond", "requires_python": null, "version": "1.2.10", "yanked": false}, "urls": [{"packagetype": "sdist", "filename": "trytond-1.2.10.tar.gz"}]}
@@ -229,7 +229,8 @@
 {"info": {"classifiers": ["Development Status :: 5 - Production/Stable", "Environment :: No Input/Output (Daemon)", "Framework :: Tryton", "Intended Audience :: Developers", "License :: OSI Approved :: GNU General Public License v3 or later (GPLv3+)", "Natural Language :: Bulgarian", "Natural Language :: Catalan", "Natural Language :: Chinese (Simplified)", "Natural Language :: Czech", "Natural Language :: Dutch", "Natural Language :: English", "Natural Language :: French", "Natural Language :: German", "Natural Language :: Hungarian", "Natural Language :: Italian", "Natural Language :: Persian", "Natural Language :: Polish", "Natural Language :: Portuguese (Brazilian)", "Natural Language :: Russian", "Natural Language :: Slovenian", "Natural Language :: Spanish", "Operating System :: OS Independent", "Programming Language :: Python :: 2.7", "Programming Language :: Python :: 3.4", "Programming Language :: Python :: 3.5", "Programming Language :: Python :: 3.6", "Programming Language :: Python :: Implementation :: CPython", "Programming Language :: Python :: Implementation :: PyPy", "Topic :: Software Development :: Libraries :: Application Frameworks"], "name": "trytond", "requires_python": "", "version": "4.8.18", "yanked": false}, "urls": [{"packagetype": "bdist_wheel", "filename": "trytond-4.8.18-py2-none-any.whl"}, {"packagetype": "bdist_wheel", "filename": "trytond-4.8.18-py3-none-any.whl"}, {"packagetype": "sdist", "filename": "trytond-4.8.18.tar.gz"}]}
 {"info": {"classifiers": ["Development Status :: 5 - Production/Stable", "Environment :: Console", "Environment :: No Input/Output (Daemon)", "Framework :: Tryton", "Intended Audience :: Developers", "License :: OSI Approved :: GNU General Public License v3 or later (GPLv3+)", "Natural Language :: Bulgarian", "Natural Language :: Catalan", "Natural Language :: Chinese (Simplified)", "Natural Language :: Czech", "Natural Language :: Dutch", "Natural Language :: English", "Natural Language :: Finnish", "Natural Language :: French", "Natural Language :: German", "Natural Language :: Hungarian", "Natural Language :: Indonesian", "Natural Language :: Italian", "Natural Language :: Persian", "Natural Language :: Polish", "Natural Language :: Portuguese (Brazilian)", "Natural Language :: Russian", "Natural Language :: Slovenian", "Natural Language :: Spanish", "Natural Language :: Turkish", "Operating System :: OS Independent", "Programming Language :: Python :: 3", "Programming Language :: Python :: 3.6", "Programming Language :: Python :: 3.7", "Programming Language :: Python :: 3.8", "Programming Language :: Python :: Implementation :: CPython", "Programming Language :: Python :: Implementation :: PyPy", "Topic :: Software Development :: Libraries :: Application Frameworks"], "name": "trytond", "requires_python": ">=3.6", "version": "5.8.16", "yanked": false}, "urls": [{"packagetype": "bdist_wheel", "filename": "trytond-5.8.16-py3-none-any.whl"}, {"packagetype": "sdist", "filename": "trytond-5.8.16.tar.gz"}]}
 {"info": {"classifiers": ["Development Status :: 5 - Production/Stable", "Environment :: Console", "Environment :: No Input/Output (Daemon)", "Framework :: Tryton", "Intended Audience :: Developers", "License :: OSI Approved :: GNU General Public License v3 or later (GPLv3+)", "Natural Language :: Bulgarian", "Natural Language :: Catalan", "Natural Language :: Chinese (Simplified)", "Natural Language :: Czech", "Natural Language :: Dutch", "Natural Language :: English", "Natural Language :: Finnish", "Natural Language :: French", "Natural Language :: German", "Natural Language :: Hungarian", "Natural Language :: Indonesian", "Natural Language :: Italian", "Natural Language :: Persian", "Natural Language :: Polish", "Natural Language :: Portuguese (Brazilian)", "Natural Language :: Romanian", "Natural Language :: Russian", "Natural Language :: Slovenian", "Natural Language :: Spanish", "Natural Language :: Turkish", "Natural Language :: Ukrainian", "Operating System :: OS Independent", "Programming Language :: Python :: 3", "Programming Language :: Python :: 3.10", "Programming Language :: Python :: 3.11", "Programming Language :: Python :: 3.8", "Programming Language :: Python :: 3.9", "Programming Language :: Python :: Implementation :: CPython", "Topic :: Software Development :: Libraries :: Application Frameworks"], "name": "trytond", "requires_python": ">=3.8", "version": "6.8.17", "yanked": false}, "urls": [{"packagetype": "bdist_wheel", "filename": "trytond-6.8.17-py3-none-any.whl"}, {"packagetype": "sdist", "filename": "trytond-6.8.17.tar.gz"}]}
-{"info": {"classifiers": ["Development Status :: 5 - Production/Stable", "Environment :: Console", "Environment :: No Input/Output (Daemon)", "Framework :: Tryton", "Intended Audience :: Developers", "License :: OSI Approved :: GNU General Public License v3 or later (GPLv3+)", "Natural Language :: Bulgarian", "Natural Language :: Catalan", "Natural Language :: Chinese (Simplified)", "Natural Language :: Czech", "Natural Language :: Dutch", "Natural Language :: English", "Natural Language :: Finnish", "Natural Language :: French", "Natural Language :: German", "Natural Language :: Hungarian", "Natural Language :: Indonesian", "Natural Language :: Italian", "Natural Language :: Persian", "Natural Language :: Polish", "Natural Language :: Portuguese (Brazilian)", "Natural Language :: Romanian", "Natural Language :: Russian", "Natural Language :: Slovenian", "Natural Language :: Spanish", "Natural Language :: Turkish", "Natural Language :: Ukrainian", "Operating System :: OS Independent", "Programming Language :: Python :: 3", "Programming Language :: Python :: 3.10", "Programming Language :: Python :: 3.11", "Programming Language :: Python :: 3.12", "Programming Language :: Python :: 3.13", "Programming Language :: Python :: 3.9", "Programming Language :: Python :: Implementation :: CPython", "Topic :: Software Development :: Libraries :: Application Frameworks"], "name": "trytond", "requires_python": ">=3.9", "version": "7.8.0", "yanked": false}, "urls": [{"packagetype": "bdist_wheel", "filename": "trytond-7.8.0-py3-none-any.whl"}, {"packagetype": "sdist", "filename": "trytond-7.8.0.tar.gz"}]}
+{"info": {"classifiers": ["Development Status :: 5 - Production/Stable", "Environment :: Console", "Environment :: No Input/Output (Daemon)", "Framework :: Tryton", "Intended Audience :: Developers", "License :: OSI Approved :: GNU General Public License v3 or later (GPLv3+)", "Natural Language :: Bulgarian", "Natural Language :: Catalan", "Natural Language :: Chinese (Simplified)", "Natural Language :: Czech", "Natural Language :: Dutch", "Natural Language :: English", "Natural Language :: Finnish", "Natural Language :: French", "Natural Language :: German", "Natural Language :: Hungarian", "Natural Language :: Indonesian", "Natural Language :: Italian", "Natural Language :: Persian", "Natural Language :: Polish", "Natural Language :: Portuguese (Brazilian)", "Natural Language :: Romanian", "Natural Language :: Russian", "Natural Language :: Slovenian", "Natural Language :: Spanish", "Natural Language :: Turkish", "Natural Language :: Ukrainian", "Operating System :: OS Independent", "Programming Language :: Python :: 3", "Programming Language :: Python :: 3.10", "Programming Language :: Python :: 3.11", "Programming Language :: Python :: 3.12", "Programming Language :: Python :: 3.13", "Programming Language :: Python :: 3.9", "Programming Language :: Python :: Implementation :: CPython", "Topic :: Software Development :: Libraries :: Application Frameworks"], "name": "trytond", "requires_python": ">=3.9", "version": "7.8.4", "yanked": false}, "urls": [{"packagetype": "bdist_wheel", "filename": "trytond-7.8.4-py3-none-any.whl"}, {"packagetype": "sdist", "filename": "trytond-7.8.4.tar.gz"}]}
 {"info": {"classifiers": ["Development Status :: 4 - Beta", "Intended Audience :: Developers", "Intended Audience :: Information Technology", "Intended Audience :: System Administrators", "License :: OSI Approved :: MIT License", "Operating System :: OS Independent", "Programming Language :: Python", "Programming Language :: Python :: 3", "Programming Language :: Python :: 3 :: Only", "Programming Language :: Python :: 3.10", "Programming Language :: Python :: 3.11", "Programming Language :: Python :: 3.12", "Programming Language :: Python :: 3.13", "Programming Language :: Python :: 3.7", "Programming Language :: Python :: 3.8", "Programming Language :: Python :: 3.9", "Topic :: Software Development", "Topic :: Software Development :: Libraries", "Topic :: Software Development :: Libraries :: Application Frameworks", "Topic :: Software Development :: Libraries :: Python Modules", "Typing :: Typed"], "name": "typer", "requires_python": ">=3.7", "version": "0.15.4", "yanked": false}, "urls": [{"packagetype": "bdist_wheel", "filename": "typer-0.15.4-py3-none-any.whl"}, {"packagetype": "sdist", "filename": "typer-0.15.4.tar.gz"}]}
-{"info": {"classifiers": ["Development Status :: 4 - Beta", "Intended Audience :: Developers", "Intended Audience :: Information Technology", "Intended Audience :: System Administrators", "License :: OSI Approved :: MIT License", "Operating System :: OS Independent", "Programming Language :: Python", "Programming Language :: Python :: 3", "Programming Language :: Python :: 3 :: Only", "Programming Language :: Python :: 3.10", "Programming Language :: Python :: 3.11", "Programming Language :: Python :: 3.12", "Programming Language :: Python :: 3.13", "Programming Language :: Python :: 3.14", "Programming Language :: Python :: 3.8", "Programming Language :: Python :: 3.9", "Topic :: Software Development", "Topic :: Software Development :: Libraries", "Topic :: Software Development :: Libraries :: Application Frameworks", "Topic :: Software Development :: Libraries :: Python Modules", "Typing :: Typed"], "name": "typer", "requires_python": ">=3.8", "version": "0.20.0", "yanked": false}, "urls": [{"packagetype": "bdist_wheel", "filename": "typer-0.20.0-py3-none-any.whl"}, {"packagetype": "sdist", "filename": "typer-0.20.0.tar.gz"}]}
+{"info": {"classifiers": ["Development Status :: 4 - Beta", "Intended Audience :: Developers", "Intended Audience :: Information Technology", "Intended Audience :: System Administrators", "Operating System :: OS Independent", "Programming Language :: Python", "Programming Language :: Python :: 3", "Programming Language :: Python :: 3 :: Only", "Programming Language :: Python :: 3.10", "Programming Language :: Python :: 3.11", "Programming Language :: Python :: 3.12", "Programming Language :: Python :: 3.13", "Programming Language :: Python :: 3.14", "Programming Language :: Python :: 3.9", "Topic :: Software Development", "Topic :: Software Development :: Libraries", "Topic :: Software Development :: Libraries :: Application Frameworks", "Topic :: Software Development :: Libraries :: Python Modules", "Typing :: Typed"], "name": "typer", "requires_python": ">=3.9", "version": "0.21.1", "yanked": false}, "urls": [{"packagetype": "bdist_wheel", "filename": "typer-0.21.1-py3-none-any.whl"}, {"packagetype": "sdist", "filename": "typer-0.21.1.tar.gz"}]}
 {"info": {"classifiers": ["Development Status :: 3 - Alpha", "Intended Audience :: Developers", "License :: OSI Approved :: BSD License", "Operating System :: OS Independent", "Programming Language :: Python", "Programming Language :: Python :: 3", "Programming Language :: Python :: 3 :: Only", "Programming Language :: Python :: 3.10", "Programming Language :: Python :: 3.11", "Programming Language :: Python :: 3.12", "Programming Language :: Python :: 3.13", "Programming Language :: Python :: 3.9", "Programming Language :: Rust"], "name": "uuid-utils", "requires_python": ">=3.9", "version": "0.12.0", "yanked": false}, "urls": [{"packagetype": "bdist_wheel", "filename": "uuid_utils-0.12.0-cp39-abi3-macosx_10_12_x86_64.macosx_11_0_arm64.macosx_10_12_universal2.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.12.0-cp39-abi3-macosx_10_12_x86_64.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.12.0-cp39-abi3-manylinux_2_17_aarch64.manylinux2014_aarch64.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.12.0-cp39-abi3-manylinux_2_17_armv7l.manylinux2014_armv7l.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.12.0-cp39-abi3-manylinux_2_17_ppc64le.manylinux2014_ppc64le.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.12.0-cp39-abi3-manylinux_2_17_x86_64.manylinux2014_x86_64.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.12.0-cp39-abi3-manylinux_2_5_i686.manylinux1_i686.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.12.0-cp39-abi3-musllinux_1_2_aarch64.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.12.0-cp39-abi3-musllinux_1_2_armv7l.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.12.0-cp39-abi3-musllinux_1_2_i686.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.12.0-cp39-abi3-musllinux_1_2_x86_64.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.12.0-cp39-abi3-win32.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.12.0-cp39-abi3-win_amd64.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.12.0-cp39-abi3-win_arm64.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.12.0-pp311-pypy311_pp73-macosx_10_12_x86_64.macosx_11_0_arm64.macosx_10_12_universal2.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.12.0-pp311-pypy311_pp73-macosx_10_12_x86_64.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.12.0-pp311-pypy311_pp73-manylinux_2_17_aarch64.manylinux2014_aarch64.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.12.0-pp311-pypy311_pp73-manylinux_2_17_armv7l.manylinux2014_armv7l.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.12.0-pp311-pypy311_pp73-manylinux_2_17_ppc64le.manylinux2014_ppc64le.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.12.0-pp311-pypy311_pp73-manylinux_2_17_x86_64.manylinux2014_x86_64.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.12.0-pp311-pypy311_pp73-manylinux_2_5_i686.manylinux1_i686.whl"}, {"packagetype": "sdist", "filename": "uuid_utils-0.12.0.tar.gz"}]}
+{"info": {"classifiers": ["Development Status :: 4 - Beta", "Intended Audience :: Developers", "License :: OSI Approved :: BSD License", "Operating System :: OS Independent", "Programming Language :: Python", "Programming Language :: Python :: 3", "Programming Language :: Python :: 3 :: Only", "Programming Language :: Python :: 3.10", "Programming Language :: Python :: 3.11", "Programming Language :: Python :: 3.12", "Programming Language :: Python :: 3.13", "Programming Language :: Python :: 3.14", "Programming Language :: Python :: 3.9", "Programming Language :: Rust"], "name": "uuid_utils", "requires_python": ">=3.9", "version": "0.14.0", "yanked": false}, "urls": [{"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.0-cp39-abi3-macosx_10_12_x86_64.macosx_11_0_arm64.macosx_10_12_universal2.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.0-cp39-abi3-macosx_10_12_x86_64.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.0-cp39-abi3-manylinux_2_17_aarch64.manylinux2014_aarch64.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.0-cp39-abi3-manylinux_2_17_armv7l.manylinux2014_armv7l.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.0-cp39-abi3-manylinux_2_17_ppc64le.manylinux2014_ppc64le.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.0-cp39-abi3-manylinux_2_17_x86_64.manylinux2014_x86_64.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.0-cp39-abi3-manylinux_2_5_i686.manylinux1_i686.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.0-cp39-abi3-musllinux_1_2_aarch64.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.0-cp39-abi3-musllinux_1_2_armv7l.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.0-cp39-abi3-musllinux_1_2_i686.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.0-cp39-abi3-musllinux_1_2_x86_64.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.0-cp39-abi3-win32.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.0-cp39-abi3-win_amd64.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.0-cp39-abi3-win_arm64.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.0-pp311-pypy311_pp73-macosx_10_12_x86_64.macosx_11_0_arm64.macosx_10_12_universal2.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.0-pp311-pypy311_pp73-macosx_10_12_x86_64.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.0-pp311-pypy311_pp73-manylinux_2_17_aarch64.manylinux2014_aarch64.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.0-pp311-pypy311_pp73-manylinux_2_17_armv7l.manylinux2014_armv7l.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.0-pp311-pypy311_pp73-manylinux_2_17_ppc64le.manylinux2014_ppc64le.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.0-pp311-pypy311_pp73-manylinux_2_17_x86_64.manylinux2014_x86_64.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.0-pp311-pypy311_pp73-manylinux_2_5_i686.manylinux1_i686.whl"}, {"packagetype": "sdist", "filename": "uuid_utils-0.14.0.tar.gz"}]}
diff --git a/scripts/populate_tox/requirements.txt b/scripts/populate_tox/requirements.txt
index 0402fac5ab..77f67f24d2 100644
--- a/scripts/populate_tox/requirements.txt
+++ b/scripts/populate_tox/requirements.txt
@@ -1,3 +1,3 @@
 jinja2
-packaging
+packaging<26.0
 requests
diff --git a/scripts/populate_tox/tox.jinja b/scripts/populate_tox/tox.jinja
index e01832abcb..7e49c2156d 100755
--- a/scripts/populate_tox/tox.jinja
+++ b/scripts/populate_tox/tox.jinja
@@ -230,3 +230,4 @@ commands =
     ruff check tests sentry_sdk
     ruff format --check tests sentry_sdk
     mypy sentry_sdk
+    python scripts/find_raise_from_none.py
diff --git a/scripts/split_tox_gh_actions/templates/base.jinja b/scripts/split_tox_gh_actions/templates/base.jinja
index 8d618d228c..c3bc528a7c 100644
--- a/scripts/split_tox_gh_actions/templates/base.jinja
+++ b/scripts/split_tox_gh_actions/templates/base.jinja
@@ -23,6 +23,9 @@ concurrency:
 
 permissions:
   contents: read
+  actions: read
+  pull-requests: write
+  statuses: write
 
 env:
   BUILD_CACHE_KEY: {% raw %}${{ github.sha }}{% endraw %}
diff --git a/scripts/split_tox_gh_actions/templates/test_group.jinja b/scripts/split_tox_gh_actions/templates/test_group.jinja
index 3e1ab30290..e9581d2d8f 100644
--- a/scripts/split_tox_gh_actions/templates/test_group.jinja
+++ b/scripts/split_tox_gh_actions/templates/test_group.jinja
@@ -42,7 +42,7 @@
     # Use Docker container only for Python 3.6
     {% raw %}container: ${{ matrix.python-version == '3.6' && 'python:3.6' || null }}{% endraw %}
     steps:
-      - uses: actions/checkout@v6.0.1
+      - uses: actions/checkout@v6.0.2
       - uses: actions/setup-python@v6
         {% raw %}if: ${{ matrix.python-version != '3.6' }}{% endraw %}
         with:
@@ -94,20 +94,11 @@
           coverage combine .coverage-sentry-*
           coverage xml
 
-      - name: Upload coverage to Codecov
+      - name: Parse and Upload Coverage
         if: {% raw %}${{ !cancelled() }}{% endraw %}
-        uses: codecov/codecov-action@v5.5.2
+        uses: getsentry/codecov-action@main
         with:
-          token: {% raw %}${{ secrets.CODECOV_TOKEN }}{% endraw %}
+          token: {% raw %}${{ secrets.GITHUB_TOKEN }}{% endraw %}
           files: coverage.xml
-          # make sure no plugins alter our coverage reports
-          plugins: noop
-          verbose: true
-
-      - name: Upload test results to Codecov
-        if: {% raw %}${{ !cancelled() }}{% endraw %}
-        uses: codecov/test-results-action@v1
-        with:
-          token: {% raw %}${{ secrets.CODECOV_TOKEN }}{% endraw %}
-          files: .junitxml
+          junit-xml-pattern: .junitxml
           verbose: true
diff --git a/sentry_sdk/_batcher.py b/sentry_sdk/_batcher.py
new file mode 100644
index 0000000000..4a6ee07e67
--- /dev/null
+++ b/sentry_sdk/_batcher.py
@@ -0,0 +1,139 @@
+import os
+import random
+import threading
+from datetime import datetime, timezone
+from typing import TYPE_CHECKING, TypeVar, Generic
+
+from sentry_sdk.utils import format_timestamp, safe_repr, serialize_attribute
+from sentry_sdk.envelope import Envelope, Item, PayloadRef
+
+if TYPE_CHECKING:
+    from typing import Optional, Callable, Any
+
+T = TypeVar("T")
+
+
+class Batcher(Generic[T]):
+    MAX_BEFORE_FLUSH = 100
+    MAX_BEFORE_DROP = 1_000
+    FLUSH_WAIT_TIME = 5.0
+
+    TYPE = ""
+    CONTENT_TYPE = ""
+
+    def __init__(
+        self,
+        capture_func: "Callable[[Envelope], None]",
+        record_lost_func: "Callable[..., None]",
+    ) -> None:
+        self._buffer: "list[T]" = []
+        self._capture_func = capture_func
+        self._record_lost_func = record_lost_func
+        self._running = True
+        self._lock = threading.Lock()
+
+        self._flush_event: "threading.Event" = threading.Event()
+
+        self._flusher: "Optional[threading.Thread]" = None
+        self._flusher_pid: "Optional[int]" = None
+
+    def _ensure_thread(self) -> bool:
+        """For forking processes we might need to restart this thread.
+        This ensures that our process actually has that thread running.
+        """
+        if not self._running:
+            return False
+
+        pid = os.getpid()
+        if self._flusher_pid == pid:
+            return True
+
+        with self._lock:
+            # Recheck to make sure another thread didn't get here and start the
+            # the flusher in the meantime
+            if self._flusher_pid == pid:
+                return True
+
+            self._flusher_pid = pid
+
+            self._flusher = threading.Thread(target=self._flush_loop)
+            self._flusher.daemon = True
+
+            try:
+                self._flusher.start()
+            except RuntimeError:
+                # Unfortunately at this point the interpreter is in a state that no
+                # longer allows us to spawn a thread and we have to bail.
+                self._running = False
+                return False
+
+        return True
+
+    def _flush_loop(self) -> None:
+        while self._running:
+            self._flush_event.wait(self.FLUSH_WAIT_TIME + random.random())
+            self._flush_event.clear()
+            self._flush()
+
+    def add(self, item: "T") -> None:
+        if not self._ensure_thread() or self._flusher is None:
+            return None
+
+        with self._lock:
+            if len(self._buffer) >= self.MAX_BEFORE_DROP:
+                self._record_lost(item)
+                return None
+
+            self._buffer.append(item)
+            if len(self._buffer) >= self.MAX_BEFORE_FLUSH:
+                self._flush_event.set()
+
+    def kill(self) -> None:
+        if self._flusher is None:
+            return
+
+        self._running = False
+        self._flush_event.set()
+        self._flusher = None
+
+    def flush(self) -> None:
+        self._flush()
+
+    def _add_to_envelope(self, envelope: "Envelope") -> None:
+        envelope.add_item(
+            Item(
+                type=self.TYPE,
+                content_type=self.CONTENT_TYPE,
+                headers={
+                    "item_count": len(self._buffer),
+                },
+                payload=PayloadRef(
+                    json={
+                        "items": [
+                            self._to_transport_format(item) for item in self._buffer
+                        ]
+                    }
+                ),
+            )
+        )
+
+    def _flush(self) -> "Optional[Envelope]":
+        envelope = Envelope(
+            headers={"sent_at": format_timestamp(datetime.now(timezone.utc))}
+        )
+        with self._lock:
+            if len(self._buffer) == 0:
+                return None
+
+            self._add_to_envelope(envelope)
+            self._buffer.clear()
+
+        self._capture_func(envelope)
+        return envelope
+
+    def _record_lost(self, item: "T") -> None:
+        pass
+
+    @staticmethod
+    def _to_transport_format(item: "T") -> "Any":
+        pass
diff --git a/sentry_sdk/_log_batcher.py b/sentry_sdk/_log_batcher.py
index 51886f48f9..1c59f7379c 100644
--- a/sentry_sdk/_log_batcher.py
+++ b/sentry_sdk/_log_batcher.py
@@ -1,164 +1,56 @@
-import os
-import random
-import threading
-from datetime import datetime, timezone
-from typing import Optional, List, Callable, TYPE_CHECKING, Any
+from typing import TYPE_CHECKING
 
-from sentry_sdk.utils import format_timestamp, safe_repr, serialize_attribute
+from sentry_sdk._batcher import Batcher
+from sentry_sdk.utils import serialize_attribute
 from sentry_sdk.envelope import Envelope, Item, PayloadRef
 
 if TYPE_CHECKING:
+    from typing import Any
     from sentry_sdk._types import Log
 
 
-class LogBatcher:
-    MAX_LOGS_BEFORE_FLUSH = 100
-    MAX_LOGS_BEFORE_DROP = 1_000
+class LogBatcher(Batcher["Log"]):
+    MAX_BEFORE_FLUSH = 100
+    MAX_BEFORE_DROP = 1_000
     FLUSH_WAIT_TIME = 5.0
 
-    def __init__(
-        self,
-        capture_func: "Callable[[Envelope], None]",
-        record_lost_func: "Callable[..., None]",
-    ) -> None:
-        self._log_buffer: "List[Log]" = []
-        self._capture_func = capture_func
-        self._record_lost_func = record_lost_func
-        self._running = True
-        self._lock = threading.Lock()
-
-        self._flush_event: "threading.Event" = threading.Event()
-
-        self._flusher: "Optional[threading.Thread]" = None
-        self._flusher_pid: "Optional[int]" = None
-
-    def _ensure_thread(self) -> bool:
-        """For forking processes we might need to restart this thread.
-        This ensures that our process actually has that thread running.
-        """
-        if not self._running:
-            return False
-
-        pid = os.getpid()
-        if self._flusher_pid == pid:
-            return True
-
-        with self._lock:
-            # Recheck to make sure another thread didn't get here and start the
-            # the flusher in the meantime
-            if self._flusher_pid == pid:
-                return True
-
-            self._flusher_pid = pid
-
-            self._flusher = threading.Thread(target=self._flush_loop)
-            self._flusher.daemon = True
-
-            try:
-                self._flusher.start()
-            except RuntimeError:
-                # Unfortunately at this point the interpreter is in a state that no
-                # longer allows us to spawn a thread and we have to bail.
-                self._running = False
-                return False
-
-        return True
-
-    def _flush_loop(self) -> None:
-        while self._running:
-            self._flush_event.wait(self.FLUSH_WAIT_TIME + random.random())
-            self._flush_event.clear()
-            self._flush()
-
-    def add(
-        self,
-        log: "Log",
-    ) -> None:
-        if not self._ensure_thread() or self._flusher is None:
-            return None
-
-        with self._lock:
-            if len(self._log_buffer) >= self.MAX_LOGS_BEFORE_DROP:
-                # Construct log envelope item without sending it to report lost bytes
-                log_item = Item(
-                    type="log",
-                    content_type="application/vnd.sentry.items.log+json",
-                    headers={
-                        "item_count": 1,
-                    },
-                    payload=PayloadRef(
-                        json={"items": [LogBatcher._log_to_transport_format(log)]}
-                    ),
-                )
-                self._record_lost_func(
-                    reason="queue_overflow",
-                    data_category="log_item",
-                    item=log_item,
-                    quantity=1,
-                )
-                return None
-
-            self._log_buffer.append(log)
-            if len(self._log_buffer) >= self.MAX_LOGS_BEFORE_FLUSH:
-                self._flush_event.set()
-
-    def kill(self) -> None:
-        if self._flusher is None:
-            return
-
-        self._running = False
-        self._flush_event.set()
-        self._flusher = None
-
-    def flush(self) -> None:
-        self._flush()
+    TYPE = "log"
+    CONTENT_TYPE = "application/vnd.sentry.items.log+json"
 
     @staticmethod
-    def _log_to_transport_format(log: "Log") -> "Any":
-        if "sentry.severity_number" not in log["attributes"]:
-            log["attributes"]["sentry.severity_number"] = log["severity_number"]
-        if "sentry.severity_text" not in log["attributes"]:
-            log["attributes"]["sentry.severity_text"] = log["severity_text"]
+    def _to_transport_format(item: "Log") -> "Any":
+        if "sentry.severity_number" not in item["attributes"]:
+            item["attributes"]["sentry.severity_number"] = item["severity_number"]
+        if "sentry.severity_text" not in item["attributes"]:
+            item["attributes"]["sentry.severity_text"] = item["severity_text"]
 
         res = {
-            "timestamp": int(log["time_unix_nano"]) / 1.0e9,
-            "trace_id": log.get("trace_id", "00000000-0000-0000-0000-000000000000"),
-            "span_id": log.get("span_id"),
-            "level": str(log["severity_text"]),
-            "body": str(log["body"]),
+            "timestamp": int(item["time_unix_nano"]) / 1.0e9,
+            "trace_id": item.get("trace_id", "00000000-0000-0000-0000-000000000000"),
+            "span_id": item.get("span_id"),
+            "level": str(item["severity_text"]),
+            "body": str(item["body"]),
             "attributes": {
-                k: serialize_attribute(v) for (k, v) in log["attributes"].items()
+                k: serialize_attribute(v) for (k, v) in item["attributes"].items()
             },
         }
 
         return res
 
-    def _flush(self) -> "Optional[Envelope]":
-        envelope = Envelope(
-            headers={"sent_at": format_timestamp(datetime.now(timezone.utc))}
+    def _record_lost(self, item: "Log") -> None:
+        # Construct log envelope item without sending it to report lost bytes
+        log_item = Item(
+            type=self.TYPE,
+            content_type=self.CONTENT_TYPE,
+            headers={
+                "item_count": 1,
+            },
+            payload=PayloadRef(json={"items": [self._to_transport_format(item)]}),
         )
-        with self._lock:
-            if len(self._log_buffer) == 0:
-                return None
 
-            envelope.add_item(
-                Item(
-                    type="log",
-                    content_type="application/vnd.sentry.items.log+json",
-                    headers={
-                        "item_count": len(self._log_buffer),
-                    },
-                    payload=PayloadRef(
-                        json={
-                            "items": [
-                                self._log_to_transport_format(log)
-                                for log in self._log_buffer
-                            ]
-                        }
-                    ),
-                )
-            )
-            self._log_buffer.clear()
-
-        self._capture_func(envelope)
-        return envelope
+        self._record_lost_func(
+            reason="queue_overflow",
+            data_category="log_item",
+            item=log_item,
+            quantity=1,
+        )
diff --git a/sentry_sdk/_metrics_batcher.py b/sentry_sdk/_metrics_batcher.py
index 6cbac0cbce..e60a4c86ec 100644
--- a/sentry_sdk/_metrics_batcher.py
+++ b/sentry_sdk/_metrics_batcher.py
@@ -1,146 +1,46 @@
-import os
-import random
-import threading
-from datetime import datetime, timezone
-from typing import Optional, List, Callable, TYPE_CHECKING, Any, Union
+from typing import TYPE_CHECKING
 
-from sentry_sdk.utils import format_timestamp, safe_repr, serialize_attribute
-from sentry_sdk.envelope import Envelope, Item, PayloadRef
+from sentry_sdk._batcher import Batcher
+from sentry_sdk.utils import serialize_attribute
+from sentry_sdk.envelope import Item
 
 if TYPE_CHECKING:
+    from typing import Any
     from sentry_sdk._types import Metric
 
 
-class MetricsBatcher:
-    MAX_METRICS_BEFORE_FLUSH = 1000
-    MAX_METRICS_BEFORE_DROP = 10_000
+class MetricsBatcher(Batcher["Metric"]):
+    MAX_BEFORE_FLUSH = 1000
+    MAX_BEFORE_DROP = 10_000
     FLUSH_WAIT_TIME = 5.0
 
-    def __init__(
-        self,
-        capture_func: "Callable[[Envelope], None]",
-        record_lost_func: "Callable[..., None]",
-    ) -> None:
-        self._metric_buffer: "List[Metric]" = []
-        self._capture_func = capture_func
-        self._record_lost_func = record_lost_func
-        self._running = True
-        self._lock = threading.Lock()
-
-        self._flush_event: "threading.Event" = threading.Event()
-
-        self._flusher: "Optional[threading.Thread]" = None
-        self._flusher_pid: "Optional[int]" = None
-
-    def _ensure_thread(self) -> bool:
-        if not self._running:
-            return False
-
-        pid = os.getpid()
-        if self._flusher_pid == pid:
-            return True
-
-        with self._lock:
-            if self._flusher_pid == pid:
-                return True
-
-            self._flusher_pid = pid
-
-            self._flusher = threading.Thread(target=self._flush_loop)
-            self._flusher.daemon = True
-
-            try:
-                self._flusher.start()
-            except RuntimeError:
-                self._running = False
-                return False
-
-        return True
-
-    def _flush_loop(self) -> None:
-        while self._running:
-            self._flush_event.wait(self.FLUSH_WAIT_TIME + random.random())
-            self._flush_event.clear()
-            self._flush()
-
-    def add(
-        self,
-        metric: "Metric",
-    ) -> None:
-        if not self._ensure_thread() or self._flusher is None:
-            return None
-
-        with self._lock:
-            if len(self._metric_buffer) >= self.MAX_METRICS_BEFORE_DROP:
-                self._record_lost_func(
-                    reason="queue_overflow",
-                    data_category="trace_metric",
-                    quantity=1,
-                )
-                return None
-
-            self._metric_buffer.append(metric)
-            if len(self._metric_buffer) >= self.MAX_METRICS_BEFORE_FLUSH:
-                self._flush_event.set()
-
-    def kill(self) -> None:
-        if self._flusher is None:
-            return
-
-        self._running = False
-        self._flush_event.set()
-        self._flusher = None
-
-    def flush(self) -> None:
-        self._flush()
+    TYPE = "trace_metric"
+    CONTENT_TYPE = "application/vnd.sentry.items.trace-metric+json"
 
     @staticmethod
-    def _metric_to_transport_format(metric: "Metric") -> "Any":
+    def _to_transport_format(item: "Metric") -> "Any":
         res = {
-            "timestamp": metric["timestamp"],
-            "trace_id": metric["trace_id"],
-            "name": metric["name"],
-            "type": metric["type"],
-            "value": metric["value"],
+            "timestamp": item["timestamp"],
+            "trace_id": item["trace_id"],
+            "name": item["name"],
+            "type": item["type"],
+            "value": item["value"],
             "attributes": {
-                k: serialize_attribute(v) for (k, v) in metric["attributes"].items()
+                k: serialize_attribute(v) for (k, v) in item["attributes"].items()
             },
         }
 
-        if metric.get("span_id") is not None:
-            res["span_id"] = metric["span_id"]
+        if item.get("span_id") is not None:
+            res["span_id"] = item["span_id"]
 
-        if metric.get("unit") is not None:
-            res["unit"] = metric["unit"]
+        if item.get("unit") is not None:
+            res["unit"] = item["unit"]
 
         return res
 
-    def _flush(self) -> "Optional[Envelope]":
-        envelope = Envelope(
-            headers={"sent_at": format_timestamp(datetime.now(timezone.utc))}
+    def _record_lost(self, item: "Metric") -> None:
+        self._record_lost_func(
+            reason="queue_overflow",
+            data_category="trace_metric",
+            quantity=1,
         )
-        with self._lock:
-            if len(self._metric_buffer) == 0:
-                return None
-
-            envelope.add_item(
-                Item(
-                    type="trace_metric",
-                    content_type="application/vnd.sentry.items.trace-metric+json",
-                    headers={
-                        "item_count": len(self._metric_buffer),
-                    },
-                    payload=PayloadRef(
-                        json={
-                            "items": [
-                                self._metric_to_transport_format(metric)
-                                for metric in self._metric_buffer
-                            ]
-                        }
-                    ),
-                )
-            )
-            self._metric_buffer.clear()
-
-        self._capture_func(envelope)
-        return envelope
diff --git a/sentry_sdk/_span_batcher.py b/sentry_sdk/_span_batcher.py
new file mode 100644
index 0000000000..38ecc8da51
--- /dev/null
+++ b/sentry_sdk/_span_batcher.py
@@ -0,0 +1,126 @@
+import threading
+from collections import defaultdict
+from datetime import datetime, timezone
+from typing import TYPE_CHECKING
+
+from sentry_sdk._batcher import Batcher
+from sentry_sdk.consts import SPANSTATUS
+from sentry_sdk.envelope import Envelope, Item, PayloadRef
+from sentry_sdk.utils import format_timestamp, serialize_attribute, safe_repr
+
+if TYPE_CHECKING:
+    from typing import Any, Callable, Optional
+    from sentry_sdk.traces import StreamedSpan
+    from sentry_sdk._types import SerializedAttributeValue
+
+
+class SpanBatcher(Batcher["StreamedSpan"]):
+    # TODO[span-first]: size-based flushes
+    # TODO[span-first]: adjust flush/drop defaults
+    MAX_BEFORE_FLUSH = 1000
+    MAX_BEFORE_DROP = 5000
+    FLUSH_WAIT_TIME = 5.0
+
+    TYPE = "span"
+    CONTENT_TYPE = "application/vnd.sentry.items.span.v2+json"
+
+    def __init__(
+        self,
+        capture_func: "Callable[[Envelope], None]",
+        record_lost_func: "Callable[..., None]",
+    ) -> None:
+        # Spans from different traces cannot be emitted in the same envelope
+        # since the envelope contains a shared trace header. That's why we bucket
+        # by trace_id, so that we can then send the buckets each in its own
+        # envelope.
+        # trace_id -> span buffer
+        self._span_buffer: dict[str, list["StreamedSpan"]] = defaultdict(list)
+        self._capture_func = capture_func
+        self._record_lost_func = record_lost_func
+        self._running = True
+        self._lock = threading.Lock()
+
+        self._flush_event: "threading.Event" = threading.Event()
+
+        self._flusher: "Optional[threading.Thread]" = None
+        self._flusher_pid: "Optional[int]" = None
+
+    def get_size(self) -> int:
+        # caller is responsible for locking before checking this
+        return sum(len(buffer) for buffer in self._span_buffer.values())
+
+    def add(self, span: "StreamedSpan") -> None:
+        if not self._ensure_thread() or self._flusher is None:
+            return None
+
+        with self._lock:
+            size = self.get_size()
+            if size >= self.MAX_BEFORE_DROP:
+                self._record_lost_func(
+                    reason="queue_overflow",
+                    data_category="span",
+                    quantity=1,
+                )
+                return None
+
+            self._span_buffer[span.trace_id].append(span)
+            if size + 1 >= self.MAX_BEFORE_FLUSH:
+                self._flush_event.set()
+
+    @staticmethod
+    def _to_transport_format(item: "StreamedSpan") -> "Any":
+        # TODO[span-first]
+        res: "dict[str, Any]" = {
+            "name": item.name,
+        }
+
+        if item._attributes:
+            res["attributes"] = {
+                k: serialize_attribute(v) for (k, v) in item._attributes.items()
+            }
+
+        return res
+
+    def _flush(self) -> None:
+        with self._lock:
+            if len(self._span_buffer) == 0:
+                return None
+
+            envelopes = []
+            for trace_id, spans in self._span_buffer.items():
+                if spans:
+                    # TODO[span-first]
+                    # dsc = spans[0].dynamic_sampling_context()
+                    dsc = None
+
+                    envelope = Envelope(
+                        headers={
+                            "sent_at": format_timestamp(datetime.now(timezone.utc)),
+                            "trace": dsc,
+                        }
+                    )
+
+                    envelope.add_item(
+                        Item(
+                            type="span",
+                            content_type="application/vnd.sentry.items.span.v2+json",
+                            headers={
+                                "item_count": len(spans),
+                            },
+                            payload=PayloadRef(
+                                json={
+                                    "items": [
+                                        self._to_transport_format(span)
+                                        for span in spans
+                                    ]
+                                }
+                            ),
+                        )
+                    )
+
+                    envelopes.append(envelope)
+
+            self._span_buffer.clear()
+
+        for envelope in envelopes:
+            self._capture_func(envelope)
diff --git a/sentry_sdk/_types.py b/sentry_sdk/_types.py
index 5a8cb936ac..ecb8abcd10 100644
--- a/sentry_sdk/_types.py
+++ b/sentry_sdk/_types.py
@@ -6,6 +6,7 @@
 
 
 SENSITIVE_DATA_SUBSTITUTE = "[Filtered]"
+BLOB_DATA_SUBSTITUTE = "[Blob substitute]"
 
 
 class AnnotatedValue:
@@ -216,9 +217,18 @@ class SDKInfo(TypedDict):
     Hint = Dict[str, Any]
 
     AttributeValue = (
-        str | bool | float | int
-        # TODO: relay support coming soon for
-        # | list[str] | list[bool] | list[float] | list[int]
+        str
+        | bool
+        | float
+        | int
+        | list[str]
+        | list[bool]
+        | list[float]
+        | list[int]
+        | tuple[str, ...]
+        | tuple[bool, ...]
+        | tuple[float, ...]
+        | tuple[int, ...]
     )
     Attributes = dict[str, AttributeValue]
 
@@ -231,11 +241,10 @@ class SDKInfo(TypedDict):
                 "boolean",
                 "double",
                 "integer",
-                # TODO: relay support coming soon for:
-                # "string[]",
-                # "boolean[]",
-                # "double[]",
-                # "integer[]",
+                "string[]",
+                "boolean[]",
+                "double[]",
+                "integer[]",
             ],
             "value": AttributeValue,
         },
@@ -255,6 +264,7 @@ class SDKInfo(TypedDict):
     )
 
     MetricType = Literal["counter", "gauge", "distribution"]
+    MetricUnit = Union[DurationUnit, InformationUnit, str]
 
     Metric = TypedDict(
         "Metric",
@@ -265,7 +275,7 @@ class SDKInfo(TypedDict):
             "name": str,
             "type": MetricType,
             "value": float,
-            "unit": Optional[str],
+            "unit": Optional[MetricUnit],
             "attributes": Attributes,
         },
     )
@@ -349,3 +359,7 @@ class SDKInfo(TypedDict):
     )
 
     HttpStatusCodeRange = Union[int, Container[int]]
+
+    class TextPart(TypedDict):
+        type: Literal["text"]
+        content: str
diff --git a/sentry_sdk/ai/__init__.py b/sentry_sdk/ai/__init__.py
index fbcb9c061d..7f0d9f92f7 100644
--- a/sentry_sdk/ai/__init__.py
+++ b/sentry_sdk/ai/__init__.py
@@ -4,4 +4,5 @@
     GEN_AI_MESSAGE_ROLE_REVERSE_MAPPING,
     normalize_message_role,
     normalize_message_roles,
+    set_conversation_id,
 )  # noqa: F401
diff --git a/sentry_sdk/ai/_openai_completions_api.py b/sentry_sdk/ai/_openai_completions_api.py
new file mode 100644
index 0000000000..8150925b21
--- /dev/null
+++ b/sentry_sdk/ai/_openai_completions_api.py
@@ -0,0 +1,48 @@
+from collections.abc import Iterable
+
+from typing import TYPE_CHECKING
+
+if TYPE_CHECKING:
+    from sentry_sdk._types import TextPart
+
+    from openai.types.chat import (
+        ChatCompletionMessageParam,
+        ChatCompletionSystemMessageParam,
+    )
+
+
+def _is_system_instruction(message: "ChatCompletionMessageParam") -> bool:
+    return isinstance(message, dict) and message.get("role") == "system"
+
+
+def _get_system_instructions(
+    messages: "Iterable[ChatCompletionMessageParam]",
+) -> "list[ChatCompletionMessageParam]":
+    if not isinstance(messages, Iterable):
+        return []
+
+    return [message for message in messages if _is_system_instruction(message)]
+
+
+def _transform_system_instructions(
+    system_instructions: "list[ChatCompletionSystemMessageParam]",
+) -> "list[TextPart]":
+    instruction_text_parts: "list[TextPart]" = []
+
+    for instruction in system_instructions:
+        if not isinstance(instruction, dict):
+            continue
+
+        content = instruction.get("content")
+
+        if isinstance(content, str):
+            instruction_text_parts.append({"type": "text", "content": content})
+
+        elif isinstance(content, list):
+            for part in content:
+                if isinstance(part, dict) and part.get("type") == "text":
+                    text = part.get("text", None)
+                    if text is not None:
+                        instruction_text_parts.append({"type": "text", "content": text})
+
+    return instruction_text_parts
diff --git a/sentry_sdk/ai/_openai_responses_api.py b/sentry_sdk/ai/_openai_responses_api.py
new file mode 100644
index 0000000000..50fddf1d2f
--- /dev/null
+++ b/sentry_sdk/ai/_openai_responses_api.py
@@ -0,0 +1,22 @@
+from typing import TYPE_CHECKING
+
+if TYPE_CHECKING:
+    from typing import Union
+
+    from openai.types.responses import ResponseInputParam, ResponseInputItemParam
+
+
+def _is_system_instruction(message: "ResponseInputItemParam") -> bool:
+    if not isinstance(message, dict) or not message.get("role") == "system":
+        return False
+
+    return "type" not in message or message["type"] == "message"
+
+
+def _get_system_instructions(
+    messages: "Union[str, ResponseInputParam]",
+) -> "list[ResponseInputItemParam]":
+    if not isinstance(messages, list):
+        return []
+
+    return [message for message in messages if _is_system_instruction(message)]
diff --git a/sentry_sdk/ai/monitoring.py b/sentry_sdk/ai/monitoring.py
index e7e00ad462..581e967bd4 100644
--- a/sentry_sdk/ai/monitoring.py
+++ b/sentry_sdk/ai/monitoring.py
@@ -1,11 +1,12 @@
 import inspect
+import sys
 from functools import wraps
 
 from sentry_sdk.consts import SPANDATA
 import sentry_sdk.utils
 from sentry_sdk import start_span
 from sentry_sdk.tracing import Span
-from sentry_sdk.utils import ContextVar
+from sentry_sdk.utils import ContextVar, reraise, capture_internal_exceptions
 
 from typing import TYPE_CHECKING
 
@@ -44,13 +45,15 @@ def sync_wrapped(*args: "Any", **kwargs: "Any") -> "Any":
                     try:
                         res = f(*args, **kwargs)
                     except Exception as e:
-                        event, hint = sentry_sdk.utils.event_from_exception(
-                            e,
-                            client_options=sentry_sdk.get_client().options,
-                            mechanism={"type": "ai_monitoring", "handled": False},
-                        )
-                        sentry_sdk.capture_event(event, hint=hint)
-                        raise e from None
+                        exc_info = sys.exc_info()
+                        with capture_internal_exceptions():
+                            event, hint = sentry_sdk.utils.event_from_exception(
+                                e,
+                                client_options=sentry_sdk.get_client().options,
+                                mechanism={"type": "ai_monitoring", "handled": False},
+                            )
+                            sentry_sdk.capture_event(event, hint=hint)
+                        reraise(*exc_info)
                     finally:
                         _ai_pipeline_name.set(None)
                     return res
@@ -72,13 +75,15 @@ async def async_wrapped(*args: "Any", **kwargs: "Any") -> "Any":
                     try:
                         res = await f(*args, **kwargs)
                     except Exception as e:
-                        event, hint = sentry_sdk.utils.event_from_exception(
-                            e,
-                            client_options=sentry_sdk.get_client().options,
-                            mechanism={"type": "ai_monitoring", "handled": False},
-                        )
-                        sentry_sdk.capture_event(event, hint=hint)
-                        raise e from None
+                        exc_info = sys.exc_info()
+                        with capture_internal_exceptions():
+                            event, hint = sentry_sdk.utils.event_from_exception(
+                                e,
+                                client_options=sentry_sdk.get_client().options,
+                                mechanism={"type": "ai_monitoring", "handled": False},
+                            )
+                            sentry_sdk.capture_event(event, hint=hint)
+                        reraise(*exc_info)
                     finally:
                         _ai_pipeline_name.set(None)
                     return res
@@ -95,6 +100,7 @@ def record_token_usage(
     span: "Span",
     input_tokens: "Optional[int]" = None,
     input_tokens_cached: "Optional[int]" = None,
+    input_tokens_cache_write: "Optional[int]" = None,
     output_tokens: "Optional[int]" = None,
     output_tokens_reasoning: "Optional[int]" = None,
     total_tokens: "Optional[int]" = None,
@@ -113,6 +119,12 @@ def record_token_usage(
             input_tokens_cached,
         )
 
+    if input_tokens_cache_write is not None:
+        span.set_data(
+            SPANDATA.GEN_AI_USAGE_INPUT_TOKENS_CACHE_WRITE,
+            input_tokens_cache_write,
+        )
+
     if output_tokens is not None:
         span.set_data(SPANDATA.GEN_AI_USAGE_OUTPUT_TOKENS, output_tokens)
 
diff --git a/sentry_sdk/ai/utils.py b/sentry_sdk/ai/utils.py
index 1d2b4483c9..684b7323da 100644
--- a/sentry_sdk/ai/utils.py
+++ b/sentry_sdk/ai/utils.py
@@ -5,6 +5,8 @@
 from sys import getsizeof
 from typing import TYPE_CHECKING
 
+from sentry_sdk._types import BLOB_DATA_SUBSTITUTE
+
 if TYPE_CHECKING:
     from typing import Any, Callable, Dict, List, Optional, Tuple
 
@@ -12,6 +14,7 @@
 
 import sentry_sdk
 from sentry_sdk.utils import logger
+from sentry_sdk.consts import SPANDATA
 
 MAX_GEN_AI_MESSAGE_BYTES = 20_000  # 20KB
 # Maximum characters when only a single message is left after bytes truncation
@@ -38,6 +41,429 @@ class GEN_AI_ALLOWED_MESSAGE_ROLES:
         GEN_AI_MESSAGE_ROLE_MAPPING[source_role] = target_role
 
 
+def parse_data_uri(url: str) -> "Tuple[str, str]":
+    """
+    Parse a data URI and return (mime_type, content).
+
+    Data URI format (RFC 2397): data:[<mediatype>][;base64],<data>
+
+    Examples:
+        data:image/jpeg;base64,/9j/4AAQ... → ("image/jpeg", "/9j/4AAQ...")
+        data:text/plain,Hello → ("text/plain", "Hello")
+        data:;base64,SGVsbG8= → ("", "SGVsbG8=")
+
+    Raises:
+        ValueError: If the URL is not a valid data URI (missing comma separator)
+    """
+    if "," not in url:
+        raise ValueError("Invalid data URI: missing comma separator")
+
+    header, content = url.split(",", 1)
+
+    # Extract mime type from header
+    # Format: "data:<mime>[;param1][;param2]..." e.g. "data:image/jpeg;base64"
+    # Remove "data:" prefix, then take everything before the first semicolon
+    if header.startswith("data:"):
+        mime_part = header[5:]  # Remove "data:" prefix
+    else:
+        mime_part = header
+
+    mime_type = mime_part.split(";")[0]
+
+    return mime_type, content
+
+
+def get_modality_from_mime_type(mime_type: str) -> str:
+    """
+    Infer the content modality from a MIME type string.
+
+    Args:
+        mime_type: A MIME type string (e.g., "image/jpeg", "audio/mp3")
+
+    Returns:
+        One of: "image", "audio", "video", or "document"
+        Defaults to "image" for unknown or empty MIME types.
+
+    Examples:
+        "image/jpeg" -> "image"
+        "audio/mp3" -> "audio"
+        "video/mp4" -> "video"
+        "application/pdf" -> "document"
+        "text/plain" -> "document"
+    """
+    if not mime_type:
+        return "image"  # Default fallback
+
+    mime_lower = mime_type.lower()
+    if mime_lower.startswith("image/"):
+        return "image"
+    elif mime_lower.startswith("audio/"):
+        return "audio"
+    elif mime_lower.startswith("video/"):
+        return "video"
+    elif mime_lower.startswith("application/") or mime_lower.startswith("text/"):
+        return "document"
+    else:
+        return "image"  # Default fallback for unknown types
+
+
+def transform_openai_content_part(
+    content_part: "Dict[str, Any]",
+) -> "Optional[Dict[str, Any]]":
+    """
+    Transform an OpenAI/LiteLLM content part to Sentry's standardized format.
+
+    This handles the OpenAI image_url format used by OpenAI and LiteLLM SDKs.
+
+    Input format:
+    - {"type": "image_url", "image_url": {"url": "..."}}
+    - {"type": "image_url", "image_url": "..."} (string shorthand)
+
+    Output format (one of):
+    - {"type": "blob", "modality": "image", "mime_type": "...", "content": "..."}
+    - {"type": "uri", "modality": "image", "mime_type": "", "uri": "..."}
+
+    Args:
+        content_part: A dictionary representing a content part from OpenAI/LiteLLM
+
+    Returns:
+        A transformed dictionary in standardized format, or None if the format
+        is not OpenAI image_url format or transformation fails.
+    """
+    if not isinstance(content_part, dict):
+        return None
+
+    block_type = content_part.get("type")
+
+    if block_type != "image_url":
+        return None
+
+    image_url_data = content_part.get("image_url")
+    if isinstance(image_url_data, str):
+        url = image_url_data
+    elif isinstance(image_url_data, dict):
+        url = image_url_data.get("url", "")
+    else:
+        return None
+
+    if not url:
+        return None
+
+    # Check if it's a data URI (base64 encoded)
+    if url.startswith("data:"):
+        try:
+            mime_type, content = parse_data_uri(url)
+            return {
+                "type": "blob",
+                "modality": get_modality_from_mime_type(mime_type),
+                "mime_type": mime_type,
+                "content": content,
+            }
+        except ValueError:
+            # If parsing fails, return as URI
+            return {
+                "type": "uri",
+                "modality": "image",
+                "mime_type": "",
+                "uri": url,
+            }
+    else:
+        # Regular URL
+        return {
+            "type": "uri",
+            "modality": "image",
+            "mime_type": "",
+            "uri": url,
+        }
+
+
+def transform_anthropic_content_part(
+    content_part: "Dict[str, Any]",
+) -> "Optional[Dict[str, Any]]":
+    """
+    Transform an Anthropic content part to Sentry's standardized format.
+
+    This handles the Anthropic image and document formats with source dictionaries.
+
+    Input format:
+    - {"type": "image", "source": {"type": "base64", "media_type": "...", "data": "..."}}
+    - {"type": "image", "source": {"type": "url", "media_type": "...", "url": "..."}}
+    - {"type": "image", "source": {"type": "file", "media_type": "...", "file_id": "..."}}
+    - {"type": "document", "source": {...}} (same source formats)
+
+    Output format (one of):
+    - {"type": "blob", "modality": "...", "mime_type": "...", "content": "..."}
+    - {"type": "uri", "modality": "...", "mime_type": "...", "uri": "..."}
+    - {"type": "file", "modality": "...", "mime_type": "...", "file_id": "..."}
+
+    Args:
+        content_part: A dictionary representing a content part from Anthropic
+
+    Returns:
+        A transformed dictionary in standardized format, or None if the format
+        is not Anthropic format or transformation fails.
+    """
+    if not isinstance(content_part, dict):
+        return None
+
+    block_type = content_part.get("type")
+
+    if block_type not in ("image", "document") or "source" not in content_part:
+        return None
+
+    source = content_part.get("source")
+    if not isinstance(source, dict):
+        return None
+
+    source_type = source.get("type")
+    media_type = source.get("media_type", "")
+    modality = (
+        "document"
+        if block_type == "document"
+        else get_modality_from_mime_type(media_type)
+    )
+
+    if source_type == "base64":
+        return {
+            "type": "blob",
+            "modality": modality,
+            "mime_type": media_type,
+            "content": source.get("data", ""),
+        }
+    elif source_type == "url":
+        return {
+            "type": "uri",
+            "modality": modality,
+            "mime_type": media_type,
+            "uri": source.get("url", ""),
+        }
+    elif source_type == "file":
+        return {
+            "type": "file",
+            "modality": modality,
+            "mime_type": media_type,
+            "file_id": source.get("file_id", ""),
+        }
+
+    return None
+
+
+def transform_google_content_part(
+    content_part: "Dict[str, Any]",
+) -> "Optional[Dict[str, Any]]":
+    """
+    Transform a Google GenAI content part to Sentry's standardized format.
+
+    This handles the Google GenAI inline_data and file_data formats.
+
+    Input format:
+    - {"inline_data": {"mime_type": "...", "data": "..."}}
+    - {"file_data": {"mime_type": "...", "file_uri": "..."}}
+
+    Output format (one of):
+    - {"type": "blob", "modality": "...", "mime_type": "...", "content": "..."}
+    - {"type": "uri", "modality": "...", "mime_type": "...", "uri": "..."}
+
+    Args:
+        content_part: A dictionary representing a content part from Google GenAI
+
+    Returns:
+        A transformed dictionary in standardized format, or None if the format
+        is not Google format or transformation fails.
+    """
+    if not isinstance(content_part, dict):
+        return None
+
+    # Handle Google inline_data format
+    if "inline_data" in content_part:
+        inline_data = content_part.get("inline_data")
+        if isinstance(inline_data, dict):
+            mime_type = inline_data.get("mime_type", "")
+            return {
+                "type": "blob",
+                "modality": get_modality_from_mime_type(mime_type),
+                "mime_type": mime_type,
+                "content": inline_data.get("data", ""),
+            }
+        return None
+
+    # Handle Google file_data format
+    if "file_data" in content_part:
+        file_data = content_part.get("file_data")
+        if isinstance(file_data, dict):
+            mime_type = file_data.get("mime_type", "")
+            return {
+                "type": "uri",
+                "modality": get_modality_from_mime_type(mime_type),
+                "mime_type": mime_type,
+                "uri": file_data.get("file_uri", ""),
+            }
+        return None
+
+    return None
+
+
+def transform_generic_content_part(
+    content_part: "Dict[str, Any]",
+) -> "Optional[Dict[str, Any]]":
+    """
+    Transform a generic/LangChain-style content part to Sentry's standardized format.
+
+    This handles generic formats where the type indicates the modality and
+    the data is provided via direct base64, url, or file_id fields.
+
+    Input format:
+    - {"type": "image", "base64": "...", "mime_type": "..."}
+    - {"type": "audio", "url": "...", "mime_type": "..."}
+    - {"type": "video", "base64": "...", "mime_type": "..."}
+    - {"type": "file", "file_id": "...", "mime_type": "..."}
+
+    Output format (one of):
+    - {"type": "blob", "modality": "...", "mime_type": "...", "content": "..."}
+    - {"type": "uri", "modality": "...", "mime_type": "...", "uri": "..."}
+    - {"type": "file", "modality": "...", "mime_type": "...", "file_id": "..."}
+
+    Args:
+        content_part: A dictionary representing a content part in generic format
+
+    Returns:
+        A transformed dictionary in standardized format, or None if the format
+        is not generic format or transformation fails.
+    """
+    if not isinstance(content_part, dict):
+        return None
+
+    block_type = content_part.get("type")
+
+    if block_type not in ("image", "audio", "video", "file"):
+        return None
+
+    # Ensure it's not Anthropic format (which also uses type: "image")
+    if "source" in content_part:
+        return None
+
+    mime_type = content_part.get("mime_type", "")
+    modality = block_type if block_type != "file" else "document"
+
+    # Check for base64 encoded content
+    if "base64" in content_part:
+        return {
+            "type": "blob",
+            "modality": modality,
+            "mime_type": mime_type,
+            "content": content_part.get("base64", ""),
+        }
+    # Check for URL reference
+    elif "url" in content_part:
+        return {
+            "type": "uri",
+            "modality": modality,
+            "mime_type": mime_type,
+            "uri": content_part.get("url", ""),
+        }
+    # Check for file_id reference
+    elif "file_id" in content_part:
+        return {
+            "type": "file",
+            "modality": modality,
+            "mime_type": mime_type,
+            "file_id": content_part.get("file_id", ""),
+        }
+
+    return None
+
+
+def transform_content_part(
+    content_part: "Dict[str, Any]",
+) -> "Optional[Dict[str, Any]]":
+    """
+    Transform a content part from various AI SDK formats to Sentry's standardized format.
+
+    This is a heuristic dispatcher that detects the format and delegates to the
+    appropriate SDK-specific transformer. For direct SDK integration, prefer using
+    the specific transformers directly:
+    - transform_openai_content_part() for OpenAI/LiteLLM
+    - transform_anthropic_content_part() for Anthropic
+    - transform_google_content_part() for Google GenAI
+    - transform_generic_content_part() for LangChain and other generic formats
+
+    Detection order:
+    1. OpenAI: type == "image_url"
+    2. Google: "inline_data" or "file_data" keys present
+    3. Anthropic: type in ("image", "document") with "source" key
+    4. Generic: type in ("image", "audio", "video", "file") with base64/url/file_id
+
+    Output format (one of):
+    - {"type": "blob", "modality": "...", "mime_type": "...", "content": "..."}
+    - {"type": "uri", "modality": "...", "mime_type": "...", "uri": "..."}
+    - {"type": "file", "modality": "...", "mime_type": "...", "file_id": "..."}
+
+    Args:
+        content_part: A dictionary representing a content part from an AI SDK
+
+    Returns:
+        A transformed dictionary in standardized format, or None if the format
+        is unrecognized or transformation fails.
+    """
+    if not isinstance(content_part, dict):
+        return None
+
+    # Try OpenAI format first (most common, clear indicator)
+    result = transform_openai_content_part(content_part)
+    if result is not None:
+        return result
+
+    # Try Google format (unique keys make it easy to detect)
+    result = transform_google_content_part(content_part)
+    if result is not None:
+        return result
+
+    # Try Anthropic format (has "source" key)
+    result = transform_anthropic_content_part(content_part)
+    if result is not None:
+        return result
+
+    # Try generic format as fallback
+    result = transform_generic_content_part(content_part)
+    if result is not None:
+        return result
+
+    # Unrecognized format
+    return None
+
+
+def transform_message_content(content: "Any") -> "Any":
+    """
+    Transform message content, handling both string content and list of content blocks.
+
+    For list content, each item is transformed using transform_content_part().
+    Items that cannot be transformed (return None) are kept as-is.
+
+    Args:
+        content: Message content - can be a string, list of content blocks, or other
+
+    Returns:
+        - String content: returned as-is
+        - List content: list with each transformable item converted to standardized format
+        - Other: returned as-is
+    """
+    if isinstance(content, str):
+        return content
+
+    if isinstance(content, (list, tuple)):
+        transformed = []
+        for item in content:
+            if isinstance(item, dict):
+                result = transform_content_part(item)
+                # If transformation succeeded, use the result; otherwise keep original
+                transformed.append(result if result is not None else item)
+            else:
+                transformed.append(item)
+        return transformed
+
+    return content
+
+
 def _normalize_data(data: "Any", unpack: bool = True) -> "Any":
     # convert pydantic data (e.g. OpenAI v1+) to json compatible format
     if hasattr(data, "model_dump"):
@@ -141,6 +567,85 @@ def _find_truncation_index(messages: "List[Dict[str, Any]]", max_bytes: int) ->
     return 0
 
 
+def redact_blob_message_parts(
+    messages: "List[Dict[str, Any]]",
+) -> "List[Dict[str, Any]]":
+    """
+    Redact blob message parts from the messages by replacing blob content with "[Filtered]".
+
+    This function creates a deep copy of messages that contain blob content to avoid
+    mutating the original message dictionaries. Messages without blob content are
+    returned as-is to minimize copying overhead.
+
+    e.g:
+    {
+        "role": "user",
+        "content": [
+            {
+                "text": "How many ponies do you see in the image?",
+                "type": "text"
+            },
+            {
+                "type": "blob",
+                "modality": "image",
+                "mime_type": "image/jpeg",
+                "content": "data:image/jpeg;base64,..."
+            }
+        ]
+    }
+    becomes:
+    {
+        "role": "user",
+        "content": [
+            {
+                "text": "How many ponies do you see in the image?",
+                "type": "text"
+            },
+            {
+                "type": "blob",
+                "modality": "image",
+                "mime_type": "image/jpeg",
+                "content": "[Filtered]"
+            }
+        ]
+    }
+    """
+
+    # First pass: check if any message contains blob content
+    has_blobs = False
+    for message in messages:
+        if not isinstance(message, dict):
+            continue
+        content = message.get("content")
+        if isinstance(content, list):
+            for item in content:
+                if isinstance(item, dict) and item.get("type") == "blob":
+                    has_blobs = True
+                    break
+        if has_blobs:
+            break
+
+    # If no blobs found, return original messages to avoid unnecessary copying
+    if not has_blobs:
+        return messages
+
+    # Deep copy messages to avoid mutating the original
+    messages_copy = deepcopy(messages)
+
+    # Second pass: redact blob content in the copy
+    for message in messages_copy:
+        if not isinstance(message, dict):
+            continue
+
+        content = message.get("content")
+        if isinstance(content, list):
+            for item in content:
+                if isinstance(item, dict) and item.get("type") == "blob":
+                    item["content"] = BLOB_DATA_SUBSTITUTE
+
+    return messages_copy
+
+
 def truncate_messages_by_size(
     messages: "List[Dict[str, Any]]",
     max_bytes: int = MAX_GEN_AI_MESSAGE_BYTES,
@@ -178,6 +683,28 @@ def truncate_messages_by_size(
 
 
 def truncate_and_annotate_messages(
+    messages: "Optional[List[Dict[str, Any]]]",
+    span: "Any",
+    scope: "Any",
+    max_single_message_chars: int = MAX_SINGLE_MESSAGE_CONTENT_CHARS,
+) -> "Optional[List[Dict[str, Any]]]":
+    if not messages:
+        return None
+
+    messages = redact_blob_message_parts(messages)
+
+    truncated_message = _truncate_single_message_content_if_present(
+        deepcopy(messages[-1]), max_chars=max_single_message_chars
+    )
+    if len(messages) > 1:
+        scope._gen_ai_original_message_count[span.span_id] = len(messages)
+
+    span.set_data(SPANDATA.META_GEN_AI_ORIGINAL_INPUT_MESSAGES_LENGTH, len(messages))
+
+    return [truncated_message]
+
+
+def truncate_and_annotate_embedding_inputs(
     messages: "Optional[List[Dict[str, Any]]]",
     span: "Any",
     scope: "Any",
@@ -186,8 +713,18 @@ def truncate_and_annotate_messages(
     if not messages:
         return None
 
+    messages = redact_blob_message_parts(messages)
+
     truncated_messages, removed_count = truncate_messages_by_size(messages, max_bytes)
     if removed_count > 0:
         scope._gen_ai_original_message_count[span.span_id] = len(messages)
 
     return truncated_messages
+
+
+def set_conversation_id(conversation_id: str) -> None:
+    """
+    Set the conversation_id in the scope.
+    """
+    scope = sentry_sdk.get_current_scope()
+    scope.set_conversation_id(conversation_id)
diff --git a/sentry_sdk/client.py b/sentry_sdk/client.py
index 259196d1c6..f540a49f35 100644
--- a/sentry_sdk/client.py
+++ b/sentry_sdk/client.py
@@ -11,6 +11,7 @@
 import sentry_sdk
 from sentry_sdk._compat import PY37, check_uwsgi_thread_support
 from sentry_sdk._metrics_batcher import MetricsBatcher
+from sentry_sdk._span_batcher import SpanBatcher
 from sentry_sdk.utils import (
     AnnotatedValue,
     ContextVar,
@@ -31,6 +32,7 @@
 )
 from sentry_sdk.serializer import serialize
 from sentry_sdk.tracing import trace
+from sentry_sdk.tracing_utils import has_span_streaming_enabled
 from sentry_sdk.transport import BaseHttpTransport, make_transport
 from sentry_sdk.consts import (
     SPANDATA,
@@ -67,6 +69,7 @@
     from sentry_sdk.scope import Scope
     from sentry_sdk.session import Session
     from sentry_sdk.spotlight import SpotlightClient
+    from sentry_sdk.traces import StreamedSpan
     from sentry_sdk.transport import Transport, Item
     from sentry_sdk._log_batcher import LogBatcher
     from sentry_sdk._metrics_batcher import MetricsBatcher
@@ -188,6 +191,8 @@ def __init__(self, options: "Optional[Dict[str, Any]]" = None) -> None:
         self.monitor: "Optional[Monitor]" = None
         self.log_batcher: "Optional[LogBatcher]" = None
         self.metrics_batcher: "Optional[MetricsBatcher]" = None
+        self.span_batcher: "Optional[SpanBatcher]" = None
+        self.integrations: "dict[str, Integration]" = {}
 
     def __getstate__(self, *args: "Any", **kwargs: "Any") -> "Any":
         return {"options": {}}
@@ -223,6 +228,9 @@ def _capture_log(self, log: "Log", scope: "Scope") -> None:
     def _capture_metric(self, metric: "Metric", scope: "Scope") -> None:
         pass
 
+    def _capture_span(self, span: "StreamedSpan", scope: "Scope") -> None:
+        pass
+
     def capture_session(self, *args: "Any", **kwargs: "Any") -> None:
         return None
 
@@ -398,6 +406,13 @@ def _record_lost_event(
                     record_lost_func=_record_lost_event,
                 )
 
+            self.span_batcher = None
+            if has_span_streaming_enabled(self.options):
+                self.span_batcher = SpanBatcher(
+                    capture_func=_capture_envelope,
+                    record_lost_func=_record_lost_event,
+                )
+
             max_request_body_size = ("always", "never", "small", "medium")
             if self.options["max_request_body_size"] not in max_request_body_size:
                 raise ValueError(
@@ -456,6 +471,8 @@ def _record_lost_event(
         if (
             self.monitor
             or self.log_batcher
+            or self.metrics_batcher
+            or self.span_batcher
             or has_profiling_enabled(self.options)
             or isinstance(self.transport, BaseHttpTransport)
         ):
@@ -526,12 +543,21 @@ def _prepare_event(
             spans_delta = spans_before - len(
                 cast(List[Dict[str, object]], event.get("spans", []))
             )
-            if is_transaction and spans_delta > 0 and self.transport is not None:
-                self.transport.record_lost_event(
-                    "event_processor", data_category="span", quantity=spans_delta
-                )
+            span_recorder_dropped_spans: int = event.pop("_dropped_spans", 0)
 
-            dropped_spans: int = event.pop("_dropped_spans", 0) + spans_delta
+            if is_transaction and self.transport is not None:
+                if spans_delta > 0:
+                    self.transport.record_lost_event(
+                        "event_processor", data_category="span", quantity=spans_delta
+                    )
+                if span_recorder_dropped_spans > 0:
+                    self.transport.record_lost_event(
+                        "buffer_overflow",
+                        data_category="span",
+                        quantity=span_recorder_dropped_spans,
+                    )
+
+            dropped_spans: int = span_recorder_dropped_spans + spans_delta
             if dropped_spans > 0:
                 previous_total_spans = spans_before + dropped_spans
             if scope._n_breadcrumbs_truncated > 0:
@@ -899,7 +925,10 @@ def capture_event(
         return return_value
 
     def _capture_telemetry(
-        self, telemetry: "Optional[Union[Log, Metric]]", ty: str, scope: "Scope"
+        self,
+        telemetry: "Optional[Union[Log, Metric, StreamedSpan]]",
+        ty: str,
+        scope: "Scope",
     ) -> None:
         # Capture attributes-based telemetry (logs, metrics, spansV2)
         if telemetry is None:
@@ -924,6 +953,8 @@ def _capture_telemetry(
             batcher = self.log_batcher
         elif ty == "metric":
             batcher = self.metrics_batcher  # type: ignore
+        elif ty == "span":
+            batcher = self.span_batcher  # type: ignore
 
         if batcher is not None:
             batcher.add(telemetry)  # type: ignore
@@ -934,6 +965,9 @@ def _capture_log(self, log: "Optional[Log]", scope: "Scope") -> None:
     def _capture_metric(self, metric: "Optional[Metric]", scope: "Scope") -> None:
         self._capture_telemetry(metric, "metric", scope)
 
+    def _capture_span(self, span: "Optional[StreamedSpan]", scope: "Scope") -> None:
+        self._capture_telemetry(span, "span", scope)
+
     def capture_session(
         self,
         session: "Session",
@@ -983,6 +1017,8 @@ def close(
                 self.log_batcher.kill()
             if self.metrics_batcher is not None:
                 self.metrics_batcher.kill()
+            if self.span_batcher is not None:
+                self.span_batcher.kill()
             if self.monitor:
                 self.monitor.kill()
             self.transport.kill()
@@ -1008,6 +1044,8 @@ def flush(
                 self.log_batcher.flush()
             if self.metrics_batcher is not None:
                 self.metrics_batcher.flush()
+            if self.span_batcher is not None:
+                self.span_batcher.flush()
             self.transport.flush(timeout=timeout, callback=callback)
 
     def __enter__(self) -> "_Client":
diff --git a/sentry_sdk/consts.py b/sentry_sdk/consts.py
index 78c3a2912f..f294414edf 100644
--- a/sentry_sdk/consts.py
+++ b/sentry_sdk/consts.py
@@ -82,6 +82,7 @@ class CompressionAlgo(Enum):
             "before_send_log": Optional[Callable[[Log, Hint], Optional[Log]]],
             "enable_metrics": Optional[bool],
             "before_send_metric": Optional[Callable[[Metric, Hint], Optional[Metric]]],
+            "trace_lifecycle": Optional[Literal["static", "stream"]],
         },
         total=False,
     )
@@ -518,6 +519,12 @@ class SPANDATA:
     Example: ["The weather in Paris is rainy and overcast, with temperatures around 57°F", "The weather in London is sunny and warm, with temperatures around 65°F"]
     """
 
+    GEN_AI_RESPONSE_TIME_TO_FIRST_TOKEN = "gen_ai.response.time_to_first_token"
+    """
+    The time it took to receive the first token from the model.
+    Example: 0.1
+    """
+
     GEN_AI_RESPONSE_TOOL_CALLS = "gen_ai.response.tool_calls"
     """
     The tool calls in the model's response.
@@ -542,6 +549,12 @@ class SPANDATA:
     Example: 2048
     """
 
+    GEN_AI_SYSTEM_INSTRUCTIONS = "gen_ai.system_instructions"
+    """
+    The system instructions passed to the model.
+    Example: [{"type": "text", "text": "You are a helpful assistant."},{"type": "text", "text": "Be concise and clear."}]
+    """
+
     GEN_AI_REQUEST_MESSAGES = "gen_ai.request.messages"
     """
     The messages passed to the model. The "content" can be a string or an array of objects.
@@ -632,6 +645,12 @@ class SPANDATA:
     Example: 50
     """
 
+    GEN_AI_USAGE_INPUT_TOKENS_CACHE_WRITE = "gen_ai.usage.input_tokens.cache_write"
+    """
+    The number of tokens written to the cache when processing the AI input (prompt).
+    Example: 100
+    """
+
     GEN_AI_USAGE_OUTPUT_TOKENS = "gen_ai.usage.output_tokens"
     """
     The number of tokens in the output.
@@ -851,6 +870,14 @@ class SPANDATA:
     Example: "a1b2c3d4e5f6"
     """
 
+    META_GEN_AI_ORIGINAL_INPUT_MESSAGES_LENGTH = (
+        "sentry.sdk_meta.gen_ai.input.messages.original_length"
+    )
+    """
+    The original number of input non-system instruction messages, before SDK trimming.
+    Example: 4
+    """
+
 
 class SPANSTATUS:
     """
@@ -1465,4 +1492,4 @@ def _get_default_options() -> "dict[str, Any]":
 del _get_default_options
 
 
-VERSION = "2.48.0"
+VERSION = "2.51.0"
diff --git a/sentry_sdk/integrations/__init__.py b/sentry_sdk/integrations/__init__.py
index 5ab181df25..dd12a6011f 100644
--- a/sentry_sdk/integrations/__init__.py
+++ b/sentry_sdk/integrations/__init__.py
@@ -81,6 +81,7 @@ def iter_default_integrations(
     "sentry_sdk.integrations.fastapi.FastApiIntegration",
     "sentry_sdk.integrations.flask.FlaskIntegration",
     "sentry_sdk.integrations.gql.GQLIntegration",
+    "sentry_sdk.integrations.google_genai.GoogleGenAIIntegration",
     "sentry_sdk.integrations.graphene.GrapheneIntegration",
     "sentry_sdk.integrations.httpx.HttpxIntegration",
     "sentry_sdk.integrations.huey.HueyIntegration",
@@ -148,6 +149,7 @@ def iter_default_integrations(
     "openai_agents": (0, 0, 19),
     "openfeature": (0, 7, 1),
     "pydantic_ai": (1, 0, 0),
+    "pymongo": (3, 5, 0),
     "quart": (0, 16, 0),
     "ray": (2, 7, 0),
     "requests": (2, 0, 0),
@@ -165,7 +167,7 @@ def iter_default_integrations(
 
 
 _INTEGRATION_DEACTIVATES = {
-    "langchain": {"openai", "anthropic"},
+    "langchain": {"openai", "anthropic", "google_genai"},
     "openai_agents": {"openai"},
     "pydantic_ai": {"openai", "anthropic"},
 }
diff --git a/sentry_sdk/integrations/anthropic.py b/sentry_sdk/integrations/anthropic.py
index 5257e3bf60..74ac71a399 100644
--- a/sentry_sdk/integrations/anthropic.py
+++ b/sentry_sdk/integrations/anthropic.py
@@ -1,3 +1,5 @@
+import sys
+import json
 from collections.abc import Iterable
 from functools import wraps
 from typing import TYPE_CHECKING
@@ -10,6 +12,7 @@
     normalize_message_roles,
     truncate_and_annotate_messages,
     get_start_span_function,
+    transform_anthropic_content_part,
 )
 from sentry_sdk.consts import OP, SPANDATA, SPANSTATUS
 from sentry_sdk.integrations import _check_minimum_version, DidNotEnable, Integration
@@ -20,6 +23,7 @@
     event_from_exception,
     package_version,
     safe_serialize,
+    reraise,
 )
 
 try:
@@ -36,13 +40,14 @@
     from anthropic.resources import AsyncMessages, Messages
 
     if TYPE_CHECKING:
-        from anthropic.types import MessageStreamEvent
+        from anthropic.types import MessageStreamEvent, TextBlockParam
 except ImportError:
     raise DidNotEnable("Anthropic not installed")
 
 if TYPE_CHECKING:
     from typing import Any, AsyncIterator, Iterator, List, Optional, Union
     from sentry_sdk.tracing import Span
+    from sentry_sdk._types import TextPart
 
 
 class AnthropicIntegration(Integration):
@@ -72,20 +77,36 @@ def _capture_exception(exc: "Any") -> None:
     sentry_sdk.capture_event(event, hint=hint)
 
 
-def _get_token_usage(result: "Messages") -> "tuple[int, int]":
+def _get_token_usage(result: "Messages") -> "tuple[int, int, int, int]":
     """
     Get token usage from the Anthropic response.
+    Returns: (input_tokens, output_tokens, cache_read_input_tokens, cache_write_input_tokens)
     """
     input_tokens = 0
     output_tokens = 0
+    cache_read_input_tokens = 0
+    cache_write_input_tokens = 0
     if hasattr(result, "usage"):
         usage = result.usage
         if hasattr(usage, "input_tokens") and isinstance(usage.input_tokens, int):
             input_tokens = usage.input_tokens
         if hasattr(usage, "output_tokens") and isinstance(usage.output_tokens, int):
             output_tokens = usage.output_tokens
-
-    return input_tokens, output_tokens
+        if hasattr(usage, "cache_read_input_tokens") and isinstance(
+            usage.cache_read_input_tokens, int
+        ):
+            cache_read_input_tokens = usage.cache_read_input_tokens
+        if hasattr(usage, "cache_creation_input_tokens") and isinstance(
+            usage.cache_creation_input_tokens, int
+        ):
+            cache_write_input_tokens = usage.cache_creation_input_tokens
+
+    return (
+        input_tokens,
+        output_tokens,
+        cache_read_input_tokens,
+        cache_write_input_tokens,
+    )
 
 
 def _collect_ai_data(
@@ -93,8 +114,10 @@ def _collect_ai_data(
     model: "str | None",
     input_tokens: int,
     output_tokens: int,
+    cache_read_input_tokens: int,
+    cache_write_input_tokens: int,
     content_blocks: "list[str]",
-) -> "tuple[str | None, int, int, list[str]]":
+) -> "tuple[str | None, int, int, int, int, list[str]]":
     """
     Collect model information, token usage, and collect content blocks from the AI streaming response.
     """
@@ -104,6 +127,14 @@ def _collect_ai_data(
                 usage = event.message.usage
                 input_tokens += usage.input_tokens
                 output_tokens += usage.output_tokens
+                if hasattr(usage, "cache_read_input_tokens") and isinstance(
+                    usage.cache_read_input_tokens, int
+                ):
+                    cache_read_input_tokens += usage.cache_read_input_tokens
+                if hasattr(usage, "cache_creation_input_tokens") and isinstance(
+                    usage.cache_creation_input_tokens, int
+                ):
+                    cache_write_input_tokens += usage.cache_creation_input_tokens
                 model = event.message.model or model
             elif event.type == "content_block_start":
                 pass
@@ -117,7 +148,56 @@ def _collect_ai_data(
             elif event.type == "message_delta":
                 output_tokens += event.usage.output_tokens
 
-    return model, input_tokens, output_tokens, content_blocks
+    return (
+        model,
+        input_tokens,
+        output_tokens,
+        cache_read_input_tokens,
+        cache_write_input_tokens,
+        content_blocks,
+    )
+
+
+def _transform_anthropic_content_block(
+    content_block: "dict[str, Any]",
+) -> "dict[str, Any]":
+    """
+    Transform an Anthropic content block using the Anthropic-specific transformer,
+    with special handling for Anthropic's text-type documents.
+    """
+    # Handle Anthropic's text-type documents specially (not covered by shared function)
+    if content_block.get("type") == "document":
+        source = content_block.get("source")
+        if isinstance(source, dict) and source.get("type") == "text":
+            return {
+                "type": "text",
+                "text": source.get("data", ""),
+            }
+
+    # Use Anthropic-specific transformation
+    result = transform_anthropic_content_part(content_block)
+    return result if result is not None else content_block
+
+
+def _transform_system_instructions(
+    system_instructions: "Union[str, Iterable[TextBlockParam]]",
+) -> "list[TextPart]":
+    if isinstance(system_instructions, str):
+        return [
+            {
+                "type": "text",
+                "content": system_instructions,
+            }
+        ]
+
+    return [
+        {
+            "type": "text",
+            "content": instruction["text"],
+        }
+        for instruction in system_instructions
+        if isinstance(instruction, dict) and "text" in instruction
+    ]
 
 
 def _set_input_data(
@@ -127,7 +207,7 @@ def _set_input_data(
     Set input data for the span based on the provided keyword arguments for the anthropic message creation.
     """
     set_data_normalized(span, SPANDATA.GEN_AI_OPERATION_NAME, "chat")
-    system_prompt = kwargs.get("system")
+    system_instructions: "Union[str, Iterable[TextBlockParam]]" = kwargs.get("system")  # type: ignore
     messages = kwargs.get("messages")
     if (
         messages is not None
@@ -135,48 +215,56 @@ def _set_input_data(
         and should_send_default_pii()
         and integration.include_prompts
     ):
-        normalized_messages = []
-        if system_prompt:
-            system_prompt_content: "Optional[Union[str, List[dict[str, Any]]]]" = None
-            if isinstance(system_prompt, str):
-                system_prompt_content = system_prompt
-            elif isinstance(system_prompt, Iterable):
-                system_prompt_content = []
-                for item in system_prompt:
-                    if (
-                        isinstance(item, dict)
-                        and item.get("type") == "text"
-                        and item.get("text")
-                    ):
-                        system_prompt_content.append(item.copy())
-
-            if system_prompt_content:
-                normalized_messages.append(
-                    {
-                        "role": GEN_AI_ALLOWED_MESSAGE_ROLES.SYSTEM,
-                        "content": system_prompt_content,
-                    }
-                )
+        if isinstance(system_instructions, str) or isinstance(
+            system_instructions, Iterable
+        ):
+            span.set_data(
+                SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS,
+                json.dumps(_transform_system_instructions(system_instructions)),
+            )
 
+        normalized_messages = []
         for message in messages:
             if (
                 message.get("role") == GEN_AI_ALLOWED_MESSAGE_ROLES.USER
                 and "content" in message
                 and isinstance(message["content"], (list, tuple))
             ):
+                transformed_content = []
                 for item in message["content"]:
-                    if item.get("type") == "tool_result":
-                        normalized_messages.append(
-                            {
-                                "role": GEN_AI_ALLOWED_MESSAGE_ROLES.TOOL,
-                                "content": {  # type: ignore[dict-item]
-                                    "tool_use_id": item.get("tool_use_id"),
-                                    "output": item.get("content"),
-                                },
-                            }
-                        )
+                    # Skip tool_result items - they can contain images/documents
+                    # with nested structures that are difficult to redact properly
+                    if isinstance(item, dict) and item.get("type") == "tool_result":
+                        continue
+
+                    # Transform content blocks (images, documents, etc.)
+                    transformed_content.append(
+                        _transform_anthropic_content_block(item)
+                        if isinstance(item, dict)
+                        else item
+                    )
+
+                # If there are non-tool-result items, add them as a message
+                if transformed_content:
+                    normalized_messages.append(
+                        {
+                            "role": message.get("role"),
+                            "content": transformed_content,
+                        }
+                    )
             else:
-                normalized_messages.append(message)
+                # Transform content for non-list messages or assistant messages
+                transformed_message = message.copy()
+                if "content" in transformed_message:
+                    content = transformed_message["content"]
+                    if isinstance(content, (list, tuple)):
+                        transformed_message["content"] = [
+                            _transform_anthropic_content_block(item)
+                            if isinstance(item, dict)
+                            else item
+                            for item in content
+                        ]
+                normalized_messages.append(transformed_message)
 
         role_normalized_messages = normalize_message_roles(normalized_messages)
         scope = sentry_sdk.get_current_scope()
@@ -219,6 +307,8 @@ def _set_output_data(
     model: "str | None",
     input_tokens: "int | None",
     output_tokens: "int | None",
+    cache_read_input_tokens: "int | None",
+    cache_write_input_tokens: "int | None",
     content_blocks: "list[Any]",
     finish_span: bool = False,
 ) -> None:
@@ -254,6 +344,8 @@ def _set_output_data(
         span,
         input_tokens=input_tokens,
         output_tokens=output_tokens,
+        input_tokens_cached=cache_read_input_tokens,
+        input_tokens_cache_write=cache_write_input_tokens,
     )
 
     if finish_span:
@@ -288,7 +380,12 @@ def _sentry_patched_create_common(f: "Any", *args: "Any", **kwargs: "Any") -> "A
 
     with capture_internal_exceptions():
         if hasattr(result, "content"):
-            input_tokens, output_tokens = _get_token_usage(result)
+            (
+                input_tokens,
+                output_tokens,
+                cache_read_input_tokens,
+                cache_write_input_tokens,
+            ) = _get_token_usage(result)
 
             content_blocks = []
             for content_block in result.content:
@@ -305,6 +402,8 @@ def _sentry_patched_create_common(f: "Any", *args: "Any", **kwargs: "Any") -> "A
                 model=getattr(result, "model", None),
                 input_tokens=input_tokens,
                 output_tokens=output_tokens,
+                cache_read_input_tokens=cache_read_input_tokens,
+                cache_write_input_tokens=cache_write_input_tokens,
                 content_blocks=content_blocks,
                 finish_span=True,
             )
@@ -317,13 +416,26 @@ def new_iterator() -> "Iterator[MessageStreamEvent]":
                 model = None
                 input_tokens = 0
                 output_tokens = 0
+                cache_read_input_tokens = 0
+                cache_write_input_tokens = 0
                 content_blocks: "list[str]" = []
 
                 for event in old_iterator:
-                    model, input_tokens, output_tokens, content_blocks = (
-                        _collect_ai_data(
-                            event, model, input_tokens, output_tokens, content_blocks
-                        )
+                    (
+                        model,
+                        input_tokens,
+                        output_tokens,
+                        cache_read_input_tokens,
+                        cache_write_input_tokens,
+                        content_blocks,
+                    ) = _collect_ai_data(
+                        event,
+                        model,
+                        input_tokens,
+                        output_tokens,
+                        cache_read_input_tokens,
+                        cache_write_input_tokens,
+                        content_blocks,
                     )
                     yield event
 
@@ -333,6 +445,8 @@ def new_iterator() -> "Iterator[MessageStreamEvent]":
                     model=model,
                     input_tokens=input_tokens,
                     output_tokens=output_tokens,
+                    cache_read_input_tokens=cache_read_input_tokens,
+                    cache_write_input_tokens=cache_write_input_tokens,
                     content_blocks=[{"text": "".join(content_blocks), "type": "text"}],
                     finish_span=True,
                 )
@@ -341,13 +455,26 @@ async def new_iterator_async() -> "AsyncIterator[MessageStreamEvent]":
                 model = None
                 input_tokens = 0
                 output_tokens = 0
+                cache_read_input_tokens = 0
+                cache_write_input_tokens = 0
                 content_blocks: "list[str]" = []
 
                 async for event in old_iterator:
-                    model, input_tokens, output_tokens, content_blocks = (
-                        _collect_ai_data(
-                            event, model, input_tokens, output_tokens, content_blocks
-                        )
+                    (
+                        model,
+                        input_tokens,
+                        output_tokens,
+                        cache_read_input_tokens,
+                        cache_write_input_tokens,
+                        content_blocks,
+                    ) = _collect_ai_data(
+                        event,
+                        model,
+                        input_tokens,
+                        output_tokens,
+                        cache_read_input_tokens,
+                        cache_write_input_tokens,
+                        content_blocks,
                     )
                     yield event
 
@@ -357,6 +484,8 @@ async def new_iterator_async() -> "AsyncIterator[MessageStreamEvent]":
                     model=model,
                     input_tokens=input_tokens,
                     output_tokens=output_tokens,
+                    cache_read_input_tokens=cache_read_input_tokens,
+                    cache_write_input_tokens=cache_write_input_tokens,
                     content_blocks=[{"text": "".join(content_blocks), "type": "text"}],
                     finish_span=True,
                 )
@@ -386,8 +515,10 @@ def _execute_sync(f: "Any", *args: "Any", **kwargs: "Any") -> "Any":
             try:
                 result = f(*args, **kwargs)
             except Exception as exc:
-                _capture_exception(exc)
-                raise exc from None
+                exc_info = sys.exc_info()
+                with capture_internal_exceptions():
+                    _capture_exception(exc)
+                reraise(*exc_info)
 
             return gen.send(result)
         except StopIteration as e:
@@ -422,8 +553,10 @@ async def _execute_async(f: "Any", *args: "Any", **kwargs: "Any") -> "Any":
             try:
                 result = await f(*args, **kwargs)
             except Exception as exc:
-                _capture_exception(exc)
-                raise exc from None
+                exc_info = sys.exc_info()
+                with capture_internal_exceptions():
+                    _capture_exception(exc)
+                reraise(*exc_info)
 
             return gen.send(result)
         except StopIteration as e:
diff --git a/sentry_sdk/integrations/arq.py b/sentry_sdk/integrations/arq.py
index ee8aa393cf..35c0a9c6f0 100644
--- a/sentry_sdk/integrations/arq.py
+++ b/sentry_sdk/integrations/arq.py
@@ -185,7 +185,7 @@ def patch_create_worker() -> None:
 
     @ensure_integration_enabled(ArqIntegration, old_create_worker)
     def _sentry_create_worker(*args: "Any", **kwargs: "Any") -> "Worker":
-        settings_cls = args[0]
+        settings_cls = args[0] if args else kwargs.get("settings_cls")
 
         if isinstance(settings_cls, dict):
             if "functions" in settings_cls:
@@ -200,13 +200,14 @@ def _sentry_create_worker(*args: "Any", **kwargs: "Any") -> "Worker":
                 ]
 
         if hasattr(settings_cls, "functions"):
-            settings_cls.functions = [
-                _get_arq_function(func) for func in settings_cls.functions
+            settings_cls.functions = [  # type: ignore[union-attr]
+                _get_arq_function(func)
+                for func in settings_cls.functions  # type: ignore[union-attr]
             ]
         if hasattr(settings_cls, "cron_jobs"):
-            settings_cls.cron_jobs = [
+            settings_cls.cron_jobs = [  # type: ignore[union-attr]
                 _get_arq_cron_job(cron_job)
-                for cron_job in (settings_cls.cron_jobs or [])
+                for cron_job in (settings_cls.cron_jobs or [])  # type: ignore[union-attr]
             ]
 
         if "functions" in kwargs:
diff --git a/sentry_sdk/integrations/asyncio.py b/sentry_sdk/integrations/asyncio.py
index 39c7e3f879..b7aa0a7202 100644
--- a/sentry_sdk/integrations/asyncio.py
+++ b/sentry_sdk/integrations/asyncio.py
@@ -4,6 +4,7 @@
 import sentry_sdk
 from sentry_sdk.consts import OP
 from sentry_sdk.integrations import Integration, DidNotEnable
+from sentry_sdk.integrations._wsgi_common import nullcontext
 from sentry_sdk.utils import event_from_exception, logger, reraise
 
 try:
@@ -47,6 +48,10 @@ def patch_asyncio() -> None:
         loop = asyncio.get_running_loop()
         orig_task_factory = loop.get_task_factory()
 
+        # Check if already patched
+        if getattr(orig_task_factory, "_is_sentry_task_factory", False):
+            return
+
         def _sentry_task_factory(
             loop: "asyncio.AbstractEventLoop",
             coro: "Coroutine[Any, Any, Any]",
@@ -56,11 +61,20 @@ def _sentry_task_factory(
             async def _task_with_sentry_span_creation() -> "Any":
                 result = None
 
+                integration = sentry_sdk.get_client().get_integration(
+                    AsyncioIntegration
+                )
+                task_spans = integration.task_spans if integration else False
+
                 with sentry_sdk.isolation_scope():
-                    with sentry_sdk.start_span(
-                        op=OP.FUNCTION,
-                        name=get_name(coro),
-                        origin=AsyncioIntegration.origin,
+                    with (
+                        sentry_sdk.start_span(
+                            op=OP.FUNCTION,
+                            name=get_name(coro),
+                            origin=AsyncioIntegration.origin,
+                        )
+                        if task_spans
+                        else nullcontext()
                     ):
                         try:
                             result = await coro
@@ -102,6 +116,7 @@ async def _task_with_sentry_span_creation() -> "Any":
 
             return task
 
+        _sentry_task_factory._is_sentry_task_factory = True  # type: ignore
         loop.set_task_factory(_sentry_task_factory)  # type: ignore
 
     except RuntimeError:
@@ -135,6 +150,54 @@ class AsyncioIntegration(Integration):
     identifier = "asyncio"
     origin = f"auto.function.{identifier}"
 
+    def __init__(self, task_spans: bool = True) -> None:
+        self.task_spans = task_spans
+
     @staticmethod
     def setup_once() -> None:
         patch_asyncio()
+
+
+def enable_asyncio_integration(*args: "Any", **kwargs: "Any") -> None:
+    """
+    Enable AsyncioIntegration with the provided options.
+
+    This is useful in scenarios where Sentry needs to be initialized before
+    an event loop is set up, but you still want to instrument asyncio once there
+    is an event loop. In that case, you can sentry_sdk.init() early on without
+    the AsyncioIntegration and then, once the event loop has been set up,
+    execute:
+
+    ```python
+    from sentry_sdk.integrations.asyncio import enable_asyncio_integration
+
+    async def async_entrypoint():
+        enable_asyncio_integration()
+    ```
+
+    Any arguments provided will be passed to AsyncioIntegration() as is.
+
+    If AsyncioIntegration has already patched the current event loop, this
+    function won't have any effect.
+
+    If AsyncioIntegration was provided in
+    sentry_sdk.init(disabled_integrations=[...]), this function will ignore that
+    and the integration will be enabled.
+    """
+    client = sentry_sdk.get_client()
+    if not client.is_active():
+        return
+
+    # This function purposefully bypasses the integration machinery in
+    # integrations/__init__.py. _installed_integrations/_processed_integrations
+    # is used to prevent double patching the same module, but in the case of
+    # the AsyncioIntegration, we don't monkeypatch the standard library directly,
+    # we patch the currently running event loop, and we keep the record of doing
+    # that on the loop itself.
+    logger.debug("Setting up integration asyncio")
+
+    integration = AsyncioIntegration(*args, **kwargs)
+    integration.setup_once()
+
+    if "asyncio" not in client.integrations:
+        client.integrations["asyncio"] = integration
diff --git a/sentry_sdk/integrations/clickhouse_driver.py b/sentry_sdk/integrations/clickhouse_driver.py
index b4cc2860e7..7bbea94210 100644
--- a/sentry_sdk/integrations/clickhouse_driver.py
+++ b/sentry_sdk/integrations/clickhouse_driver.py
@@ -30,7 +30,9 @@ def __getitem__(self, _):
 
 
 try:
-    import clickhouse_driver  # type: ignore[import-not-found]
+    from clickhouse_driver import VERSION  # type: ignore[import-not-found]
+    from clickhouse_driver.client import Client  # type: ignore[import-not-found]
+    from clickhouse_driver.connection import Connection  # type: ignore[import-not-found]
 
 except ImportError:
     raise DidNotEnable("clickhouse-driver not installed.")
@@ -42,29 +44,23 @@ class ClickhouseDriverIntegration(Integration):
 
     @staticmethod
     def setup_once() -> None:
-        _check_minimum_version(ClickhouseDriverIntegration, clickhouse_driver.VERSION)
+        _check_minimum_version(ClickhouseDriverIntegration, VERSION)
 
         # Every query is done using the Connection's `send_query` function
-        clickhouse_driver.connection.Connection.send_query = _wrap_start(
-            clickhouse_driver.connection.Connection.send_query
-        )
+        Connection.send_query = _wrap_start(Connection.send_query)
 
         # If the query contains parameters then the send_data function is used to send those parameters to clickhouse
         _wrap_send_data()
 
         # Every query ends either with the Client's `receive_end_of_query` (no result expected)
         # or its `receive_result` (result expected)
-        clickhouse_driver.client.Client.receive_end_of_query = _wrap_end(
-            clickhouse_driver.client.Client.receive_end_of_query
-        )
-        if hasattr(clickhouse_driver.client.Client, "receive_end_of_insert_query"):
+        Client.receive_end_of_query = _wrap_end(Client.receive_end_of_query)
+        if hasattr(Client, "receive_end_of_insert_query"):
             # In 0.2.7, insert queries are handled separately via `receive_end_of_insert_query`
-            clickhouse_driver.client.Client.receive_end_of_insert_query = _wrap_end(
-                clickhouse_driver.client.Client.receive_end_of_insert_query
+            Client.receive_end_of_insert_query = _wrap_end(
+                Client.receive_end_of_insert_query
             )
-        clickhouse_driver.client.Client.receive_result = _wrap_end(
-            clickhouse_driver.client.Client.receive_result
-        )
+        Client.receive_result = _wrap_end(Client.receive_result)
 
 
 P = ParamSpec("P")
@@ -128,7 +124,7 @@ def _inner_end(*args: "P.args", **kwargs: "P.kwargs") -> "T":
 
 
 def _wrap_send_data() -> None:
-    original_send_data = clickhouse_driver.client.Client.send_data
+    original_send_data = Client.send_data
 
     def _inner_send_data(  # type: ignore[no-untyped-def] # clickhouse-driver does not type send_data
         self, sample_block, data, types_check=False, columnar=False, *args, **kwargs
@@ -164,12 +160,10 @@ def wrapped_generator() -> "Iterator[Any]":
             self, sample_block, data, types_check, columnar, *args, **kwargs
         )
 
-    clickhouse_driver.client.Client.send_data = _inner_send_data
+    Client.send_data = _inner_send_data
 
 
-def _set_db_data(
-    span: "Span", connection: "clickhouse_driver.connection.Connection"
-) -> None:
+def _set_db_data(span: "Span", connection: "Connection") -> None:
     span.set_data(SPANDATA.DB_SYSTEM, "clickhouse")
     span.set_data(SPANDATA.SERVER_ADDRESS, connection.host)
     span.set_data(SPANDATA.SERVER_PORT, connection.port)
diff --git a/sentry_sdk/integrations/cohere.py b/sentry_sdk/integrations/cohere.py
index bac2ce5655..f45a02f2b5 100644
--- a/sentry_sdk/integrations/cohere.py
+++ b/sentry_sdk/integrations/cohere.py
@@ -1,3 +1,4 @@
+import sys
 from functools import wraps
 
 from sentry_sdk import consts
@@ -16,7 +17,7 @@
 import sentry_sdk
 from sentry_sdk.scope import should_send_default_pii
 from sentry_sdk.integrations import DidNotEnable, Integration
-from sentry_sdk.utils import capture_internal_exceptions, event_from_exception
+from sentry_sdk.utils import capture_internal_exceptions, event_from_exception, reraise
 
 try:
     from cohere.client import Client
@@ -151,9 +152,11 @@ def new_chat(*args: "Any", **kwargs: "Any") -> "Any":
         try:
             res = f(*args, **kwargs)
         except Exception as e:
-            _capture_exception(e)
-            span.__exit__(None, None, None)
-            raise e from None
+            exc_info = sys.exc_info()
+            with capture_internal_exceptions():
+                _capture_exception(e)
+                span.__exit__(None, None, None)
+            reraise(*exc_info)
 
         with capture_internal_exceptions():
             if should_send_default_pii() and integration.include_prompts:
@@ -247,8 +250,10 @@ def new_embed(*args: "Any", **kwargs: "Any") -> "Any":
             try:
                 res = f(*args, **kwargs)
             except Exception as e:
-                _capture_exception(e)
-                raise e from None
+                exc_info = sys.exc_info()
+                with capture_internal_exceptions():
+                    _capture_exception(e)
+                reraise(*exc_info)
             if (
                 hasattr(res, "meta")
                 and hasattr(res.meta, "billed_units")
diff --git a/sentry_sdk/integrations/django/__init__.py b/sentry_sdk/integrations/django/__init__.py
index 0cc4bc4d16..2595c33ea8 100644
--- a/sentry_sdk/integrations/django/__init__.py
+++ b/sentry_sdk/integrations/django/__init__.py
@@ -109,7 +109,7 @@ class DjangoIntegration(Integration):
     Auto instrument a Django application.
 
     :param transaction_style: How to derive transaction names. Either `"function_name"` or `"url"`. Defaults to `"url"`.
-    :param middleware_spans: Whether to create spans for middleware. Defaults to `True`.
+    :param middleware_spans: Whether to create spans for middleware. Defaults to `False`.
     :param signals_spans: Whether to create spans for signals. Defaults to `True`.
     :param signals_denylist: A list of signals to ignore when creating spans.
     :param cache_spans: Whether to create spans for cache operations. Defaults to `False`.
diff --git a/sentry_sdk/integrations/dramatiq.py b/sentry_sdk/integrations/dramatiq.py
index ae87de7525..f954d4fb98 100644
--- a/sentry_sdk/integrations/dramatiq.py
+++ b/sentry_sdk/integrations/dramatiq.py
@@ -188,6 +188,8 @@ def after_process_message(
         transaction.__exit__(type(exception), exception, None)
         scope_manager.__exit__(type(exception), exception, None)
 
+    after_skip_message = after_process_message
+
 
 def _make_message_event_processor(
     message: "Message[R]", integration: "DramatiqIntegration"
diff --git a/sentry_sdk/integrations/google_genai/utils.py b/sentry_sdk/integrations/google_genai/utils.py
index 03423c385a..b2d6499843 100644
--- a/sentry_sdk/integrations/google_genai/utils.py
+++ b/sentry_sdk/integrations/google_genai/utils.py
@@ -1,7 +1,9 @@
 import copy
+import json
 import inspect
 from functools import wraps
 from .consts import ORIGIN, TOOL_ATTRIBUTES_MAP, GEN_AI_SYSTEM
+from sentry_sdk._types import BLOB_DATA_SUBSTITUTE
 from typing import (
     cast,
     TYPE_CHECKING,
@@ -12,6 +14,7 @@
     Optional,
     Union,
     TypedDict,
+    Dict,
 )
 
 import sentry_sdk
@@ -19,6 +22,9 @@
     set_data_normalized,
     truncate_and_annotate_messages,
     normalize_message_roles,
+    redact_blob_message_parts,
+    transform_google_content_part,
+    get_modality_from_mime_type,
 )
 from sentry_sdk.consts import OP, SPANDATA
 from sentry_sdk.scope import should_send_default_pii
@@ -27,16 +33,20 @@
     event_from_exception,
     safe_serialize,
 )
-from google.genai.types import GenerateContentConfig
+from google.genai.types import GenerateContentConfig, Part, Content
+from itertools import chain
 
 if TYPE_CHECKING:
     from sentry_sdk.tracing import Span
+    from sentry_sdk._types import TextPart
     from google.genai.types import (
         GenerateContentResponse,
         ContentListUnion,
+        ContentUnionDict,
         Tool,
         Model,
         EmbedContentResponse,
+        ContentUnion,
     )
 
 
@@ -145,44 +155,326 @@ def get_model_name(model: "Union[str, Model]") -> str:
     return str(model)
 
 
-def extract_contents_text(contents: "ContentListUnion") -> "Optional[str]":
-    """Extract text from contents parameter which can have various formats."""
+def extract_contents_messages(contents: "ContentListUnion") -> "List[Dict[str, Any]]":
+    """Extract messages from contents parameter which can have various formats.
+
+    Returns a list of message dictionaries in the format:
+    - System: {"role": "system", "content": "string"}
+    - User/Assistant: {"role": "user"|"assistant", "content": [{"text": "...", "type": "text"}, ...]}
+    """
     if contents is None:
-        return None
+        return []
+
+    messages = []
 
-    # Simple string case
+    # Handle string case
     if isinstance(contents, str):
-        return contents
+        return [{"role": "user", "content": contents}]
 
-    # List of contents or parts
+    # Handle list case - process each item (non-recursive, flatten at top level)
     if isinstance(contents, list):
-        texts = []
         for item in contents:
-            # Recursively extract text from each item
-            extracted = extract_contents_text(item)
-            if extracted:
-                texts.append(extracted)
-        return " ".join(texts) if texts else None
+            item_messages = extract_contents_messages(item)
+            messages.extend(item_messages)
+        return messages
 
-    # Dictionary case
+    # Handle dictionary case (ContentDict)
     if isinstance(contents, dict):
-        if "text" in contents:
-            return contents["text"]
-        # Try to extract from parts if present in dict
-        if "parts" in contents:
-            return extract_contents_text(contents["parts"])
+        role = contents.get("role", "user")
+        parts = contents.get("parts")
+
+        if parts:
+            content_parts = []
+            tool_messages = []
+
+            for part in parts:
+                part_result = _extract_part_content(part)
+                if part_result is None:
+                    continue
+
+                if isinstance(part_result, dict) and part_result.get("role") == "tool":
+                    # Tool message - add separately
+                    tool_messages.append(part_result)
+                else:
+                    # Regular content part
+                    content_parts.append(part_result)
+
+            # Add main message if we have content parts
+            if content_parts:
+                # Normalize role: "model" -> "assistant"
+                normalized_role = "assistant" if role == "model" else role or "user"
+                messages.append({"role": normalized_role, "content": content_parts})
+
+            # Add tool messages
+            messages.extend(tool_messages)
+        elif "text" in contents:
+            # Simple text in dict
+            messages.append(
+                {
+                    "role": role or "user",
+                    "content": [{"text": contents["text"], "type": "text"}],
+                }
+            )
+
+        return messages
 
-    # Content object with parts - recurse into parts
-    if getattr(contents, "parts", None):
-        return extract_contents_text(contents.parts)
+    # Handle Content object
+    if hasattr(contents, "parts") and contents.parts:
+        role = getattr(contents, "role", None) or "user"
+        content_parts = []
+        tool_messages = []
 
-    # Direct text attribute
-    if hasattr(contents, "text"):
-        return contents.text
+        for part in contents.parts:
+            part_result = _extract_part_content(part)
+            if part_result is None:
+                continue
+
+            if isinstance(part_result, dict) and part_result.get("role") == "tool":
+                tool_messages.append(part_result)
+            else:
+                content_parts.append(part_result)
+
+        if content_parts:
+            normalized_role = "assistant" if role == "model" else role
+            messages.append({"role": normalized_role, "content": content_parts})
+
+        messages.extend(tool_messages)
+        return messages
+
+    # Handle Part object directly
+    part_result = _extract_part_content(contents)
+    if part_result:
+        if isinstance(part_result, dict) and part_result.get("role") == "tool":
+            return [part_result]
+        else:
+            return [{"role": "user", "content": [part_result]}]
+
+    # Handle PIL.Image.Image
+    try:
+        from PIL import Image as PILImage  # type: ignore[import-not-found]
+
+        if isinstance(contents, PILImage.Image):
+            blob_part = _extract_pil_image(contents)
+            if blob_part:
+                return [{"role": "user", "content": [blob_part]}]
+    except ImportError:
+        pass
+
+    # Handle File object
+    if hasattr(contents, "uri") and hasattr(contents, "mime_type"):
+        # File object
+        file_uri = getattr(contents, "uri", None)
+        mime_type = getattr(contents, "mime_type", None)
+        # Process if we have file_uri, even if mime_type is missing
+        if file_uri is not None:
+            # Default to empty string if mime_type is None
+            if mime_type is None:
+                mime_type = ""
+
+            blob_part = {
+                "type": "uri",
+                "modality": get_modality_from_mime_type(mime_type),
+                "mime_type": mime_type,
+                "uri": file_uri,
+            }
+            return [{"role": "user", "content": [blob_part]}]
+
+    # Handle direct text attribute
+    if hasattr(contents, "text") and contents.text:
+        return [
+            {"role": "user", "content": [{"text": str(contents.text), "type": "text"}]}
+        ]
+
+    return []
+
+
+def _extract_part_content(part: "Any") -> "Optional[dict[str, Any]]":
+    """Extract content from a Part object or dict.
+
+    Returns:
+        - dict for content part (text/blob) or tool message
+        - None if part should be skipped
+    """
+    if part is None:
+        return None
+
+    # Handle dict Part
+    if isinstance(part, dict):
+        # Check for function_response first (tool message)
+        if "function_response" in part:
+            return _extract_tool_message_from_part(part)
+
+        if part.get("text"):
+            return {"text": part["text"], "type": "text"}
+
+        # Try using Google-specific transform for dict formats (inline_data, file_data)
+        result = transform_google_content_part(part)
+        if result is not None:
+            # For inline_data with bytes data, substitute the content
+            if "inline_data" in part:
+                inline_data = part["inline_data"]
+                if isinstance(inline_data, dict) and isinstance(
+                    inline_data.get("data"), bytes
+                ):
+                    result["content"] = BLOB_DATA_SUBSTITUTE
+            return result
+
+        return None
+
+    # Handle Part object
+    # Check for function_response (tool message)
+    if hasattr(part, "function_response") and part.function_response:
+        return _extract_tool_message_from_part(part)
+
+    # Handle text
+    if hasattr(part, "text") and part.text:
+        return {"text": part.text, "type": "text"}
+
+    # Handle file_data
+    if hasattr(part, "file_data") and part.file_data:
+        file_data = part.file_data
+        file_uri = getattr(file_data, "file_uri", None)
+        mime_type = getattr(file_data, "mime_type", None)
+        # Process if we have file_uri, even if mime_type is missing (consistent with dict handling)
+        if file_uri is not None:
+            # Default to empty string if mime_type is None (consistent with transform_google_content_part)
+            if mime_type is None:
+                mime_type = ""
+
+            return {
+                "type": "uri",
+                "modality": get_modality_from_mime_type(mime_type),
+                "mime_type": mime_type,
+                "uri": file_uri,
+            }
+
+    # Handle inline_data
+    if hasattr(part, "inline_data") and part.inline_data:
+        inline_data = part.inline_data
+        data = getattr(inline_data, "data", None)
+        mime_type = getattr(inline_data, "mime_type", None)
+        # Process if we have data, even if mime_type is missing/empty (consistent with dict handling)
+        if data is not None:
+            # Default to empty string if mime_type is None (consistent with transform_google_content_part)
+            if mime_type is None:
+                mime_type = ""
+
+            # Handle both bytes (binary data) and str (base64-encoded data)
+            if isinstance(data, bytes):
+                content = BLOB_DATA_SUBSTITUTE
+            else:
+                # For non-bytes data (e.g., base64 strings), use as-is
+                content = data
+
+            return {
+                "type": "blob",
+                "modality": get_modality_from_mime_type(mime_type),
+                "mime_type": mime_type,
+                "content": content,
+            }
 
     return None
 
 
+def _extract_tool_message_from_part(part: "Any") -> "Optional[dict[str, Any]]":
+    """Extract tool message from a Part with function_response.
+
+    Returns:
+        {"role": "tool", "content": {"toolCallId": "...", "toolName": "...", "output": "..."}}
+        or None if not a valid tool message
+    """
+    function_response = None
+
+    if isinstance(part, dict):
+        function_response = part.get("function_response")
+    elif hasattr(part, "function_response"):
+        function_response = part.function_response
+
+    if not function_response:
+        return None
+
+    # Extract fields from function_response
+    tool_call_id = None
+    tool_name = None
+    output = None
+
+    if isinstance(function_response, dict):
+        tool_call_id = function_response.get("id")
+        tool_name = function_response.get("name")
+        response_dict = function_response.get("response", {})
+        # Prefer "output" key if present, otherwise use entire response
+        output = response_dict.get("output", response_dict)
+    else:
+        # FunctionResponse object
+        tool_call_id = getattr(function_response, "id", None)
+        tool_name = getattr(function_response, "name", None)
+        response_obj = getattr(function_response, "response", None)
+        if response_obj is None:
+            response_obj = {}
+        if isinstance(response_obj, dict):
+            output = response_obj.get("output", response_obj)
+        else:
+            output = response_obj
+
+    if not tool_name:
+        return None
+
+    return {
+        "role": "tool",
+        "content": {
+            "toolCallId": str(tool_call_id) if tool_call_id else None,
+            "toolName": str(tool_name),
+            "output": safe_serialize(output) if output is not None else None,
+        },
+    }
+
+
+def _extract_pil_image(image: "Any") -> "Optional[dict[str, Any]]":
+    """Extract blob part from PIL.Image.Image."""
+    try:
+        from PIL import Image as PILImage
+
+        if not isinstance(image, PILImage.Image):
+            return None
+
+        # Get format, default to JPEG
+        format_str = image.format or "JPEG"
+        suffix = format_str.lower()
+        mime_type = f"image/{suffix}"
+
+        return {
+            "type": "blob",
+            "modality": get_modality_from_mime_type(mime_type),
+            "mime_type": mime_type,
+            "content": BLOB_DATA_SUBSTITUTE,
+        }
+    except Exception:
+        return None
+
+
+def extract_contents_text(contents: "ContentListUnion") -> "Optional[str]":
+    """Extract text from contents parameter which can have various formats.
+
+    This is a compatibility function that extracts text from messages.
+    For new code, use extract_contents_messages instead.
+    """
+    messages = extract_contents_messages(contents)
+    if not messages:
+        return None
+
+    texts = []
+    for message in messages:
+        content = message.get("content")
+        if isinstance(content, str):
+            texts.append(content)
+        elif isinstance(content, list):
+            for part in content:
+                if isinstance(part, dict) and part.get("type") == "text":
+                    texts.append(part.get("text", ""))
+
+    return " ".join(texts) if texts else None
+
+
 def _format_tools_for_span(
     tools: "Iterable[Tool | Callable[..., Any]]",
 ) -> "Optional[List[dict[str, Any]]]":
@@ -433,6 +725,62 @@ def extract_finish_reasons(
     return finish_reasons if finish_reasons else None
 
 
+def _transform_system_instruction_one_level(
+    system_instructions: "Union[ContentUnionDict, ContentUnion]",
+    can_be_content: bool,
+) -> "list[TextPart]":
+    text_parts: "list[TextPart]" = []
+
+    if isinstance(system_instructions, str):
+        return [{"type": "text", "content": system_instructions}]
+
+    if isinstance(system_instructions, Part) and system_instructions.text:
+        return [{"type": "text", "content": system_instructions.text}]
+
+    if can_be_content and isinstance(system_instructions, Content):
+        if isinstance(system_instructions.parts, list):
+            for part in system_instructions.parts:
+                if isinstance(part.text, str):
+                    text_parts.append({"type": "text", "content": part.text})
+        return text_parts
+
+    if isinstance(system_instructions, dict) and system_instructions.get("text"):
+        return [{"type": "text", "content": system_instructions["text"]}]
+
+    elif can_be_content and isinstance(system_instructions, dict):
+        parts = system_instructions.get("parts", [])
+        for part in parts:
+            if isinstance(part, Part) and isinstance(part.text, str):
+                text_parts.append({"type": "text", "content": part.text})
+            elif isinstance(part, dict) and isinstance(part.get("text"), str):
+                text_parts.append({"type": "text", "content": part["text"]})
+        return text_parts
+
+    return text_parts
+
+
+def _transform_system_instructions(
+    system_instructions: "Union[ContentUnionDict, ContentUnion]",
+) -> "list[TextPart]":
+    text_parts: "list[TextPart]" = []
+
+    if isinstance(system_instructions, list):
+        text_parts = list(
+            chain.from_iterable(
+                _transform_system_instruction_one_level(
+                    instructions, can_be_content=False
+                )
+                for instructions in system_instructions
+            )
+        )
+
+        return text_parts
+
+    return _transform_system_instruction_one_level(
+        system_instructions, can_be_content=True
+    )
+
+
 def set_span_data_for_request(
     span: "Span",
     integration: "Any",
@@ -454,17 +802,21 @@ def set_span_data_for_request(
         messages = []
 
         # Add system instruction if present
+        system_instructions = None
         if config and hasattr(config, "system_instruction"):
-            system_instruction = config.system_instruction
-            if system_instruction:
-                system_text = extract_contents_text(system_instruction)
-                if system_text:
-                    messages.append({"role": "system", "content": system_text})
-
-        # Add user message
-        contents_text = extract_contents_text(contents)
-        if contents_text:
-            messages.append({"role": "user", "content": contents_text})
+            system_instructions = config.system_instruction
+        elif isinstance(config, dict) and "system_instruction" in config:
+            system_instructions = config.get("system_instruction")
+
+        if system_instructions is not None:
+            span.set_data(
+                SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS,
+                json.dumps(_transform_system_instructions(system_instructions)),
+            )
+
+        # Extract messages from contents
+        contents_messages = extract_contents_messages(contents)
+        messages.extend(contents_messages)
 
         if messages:
             normalized_messages = normalize_message_roles(messages)
diff --git a/sentry_sdk/integrations/gql.py b/sentry_sdk/integrations/gql.py
index 083ceaf517..c19a518f46 100644
--- a/sentry_sdk/integrations/gql.py
+++ b/sentry_sdk/integrations/gql.py
@@ -95,18 +95,23 @@ def _request_info_from_transport(
 def _patch_execute() -> None:
     real_execute = gql.Client.execute
 
+    # Maintain signature for backwards compatibility.
+    # gql.Client.execute() accepts a positional-only "request"
+    # parameter with version 4.0.0.
     @ensure_integration_enabled(GQLIntegration, real_execute)
     def sentry_patched_execute(
         self: "gql.Client",
-        document_or_request: "DocumentNode",
+        document: "DocumentNode",
         *args: "Any",
         **kwargs: "Any",
     ) -> "Any":
         scope = sentry_sdk.get_isolation_scope()
-        scope.add_event_processor(_make_gql_event_processor(self, document_or_request))
+        # document is a gql.GraphQLRequest with gql v4.0.0.
+        scope.add_event_processor(_make_gql_event_processor(self, document))
 
         try:
-            return real_execute(self, document_or_request, *args, **kwargs)
+            # document is a gql.GraphQLRequest with gql v4.0.0.
+            return real_execute(self, document, *args, **kwargs)
         except TransportQueryError as e:
             event, hint = event_from_exception(
                 e,
diff --git a/sentry_sdk/integrations/grpc/__init__.py b/sentry_sdk/integrations/grpc/__init__.py
index b6641163a9..a41631c37e 100644
--- a/sentry_sdk/integrations/grpc/__init__.py
+++ b/sentry_sdk/integrations/grpc/__init__.py
@@ -50,14 +50,29 @@ def __getitem__(self, _):
 GRPC_VERSION = parse_version(grpc.__version__)
 
 
+def _is_channel_intercepted(channel: "Channel") -> bool:
+    interceptor = getattr(channel, "_interceptor", None)
+    while interceptor is not None:
+        if isinstance(interceptor, ClientInterceptor):
+            return True
+
+        inner_channel = getattr(channel, "_channel", None)
+        if inner_channel is None:
+            return False
+
+        channel = inner_channel
+        interceptor = getattr(channel, "_interceptor", None)
+
+    return False
+
+
 def _wrap_channel_sync(func: "Callable[P, Channel]") -> "Callable[P, Channel]":
     "Wrapper for synchronous secure and insecure channel."
 
     @wraps(func)
     def patched_channel(*args: "Any", **kwargs: "Any") -> "Channel":
         channel = func(*args, **kwargs)
-        if not ClientInterceptor._is_intercepted:
-            ClientInterceptor._is_intercepted = True
+        if not _is_channel_intercepted(channel):
             return intercept_channel(channel, ClientInterceptor())
         else:
             return channel
@@ -70,7 +85,7 @@ def _wrap_intercept_channel(func: "Callable[P, Channel]") -> "Callable[P, Channe
     def patched_intercept_channel(
         channel: "Channel", *interceptors: "grpc.ServerInterceptor"
     ) -> "Channel":
-        if ClientInterceptor._is_intercepted:
+        if _is_channel_intercepted(channel):
             interceptors = tuple(
                 [
                     interceptor
diff --git a/sentry_sdk/integrations/grpc/client.py b/sentry_sdk/integrations/grpc/client.py
index 69b3f3d318..b6cbc54f10 100644
--- a/sentry_sdk/integrations/grpc/client.py
+++ b/sentry_sdk/integrations/grpc/client.py
@@ -22,8 +22,6 @@ class ClientInterceptor(
     grpc.UnaryUnaryClientInterceptor,  # type: ignore
     grpc.UnaryStreamClientInterceptor,  # type: ignore
 ):
-    _is_intercepted = False
-
     def intercept_unary_unary(
         self: "ClientInterceptor",
         continuation: "Callable[[ClientCallDetails, Message], _UnaryOutcome]",
diff --git a/sentry_sdk/integrations/httpx.py b/sentry_sdk/integrations/httpx.py
index 38e9c1a3d7..38c4f437bc 100644
--- a/sentry_sdk/integrations/httpx.py
+++ b/sentry_sdk/integrations/httpx.py
@@ -4,9 +4,9 @@
 from sentry_sdk.integrations import Integration, DidNotEnable
 from sentry_sdk.tracing import BAGGAGE_HEADER_NAME
 from sentry_sdk.tracing_utils import (
-    Baggage,
     should_propagate_trace,
     add_http_request_source,
+    add_sentry_baggage_to_headers,
 )
 from sentry_sdk.utils import (
     SENSITIVE_DATA_SUBSTITUTE,
@@ -19,7 +19,6 @@
 from typing import TYPE_CHECKING
 
 if TYPE_CHECKING:
-    from collections.abc import MutableMapping
     from typing import Any
 
 
@@ -81,7 +80,7 @@ def send(self: "Client", request: "Request", **kwargs: "Any") -> "Response":
                     )
 
                     if key == BAGGAGE_HEADER_NAME:
-                        _add_sentry_baggage_to_headers(request.headers, value)
+                        add_sentry_baggage_to_headers(request.headers, value)
                     else:
                         request.headers[key] = value
 
@@ -155,22 +154,3 @@ async def send(
         return rv
 
     AsyncClient.send = send
-
-
-def _add_sentry_baggage_to_headers(
-    headers: "MutableMapping[str, str]", sentry_baggage: str
-) -> None:
-    """Add the Sentry baggage to the headers.
-
-    This function directly mutates the provided headers. The provided sentry_baggage
-    is appended to the existing baggage. If the baggage already contains Sentry items,
-    they are stripped out first.
-    """
-    existing_baggage = headers.get(BAGGAGE_HEADER_NAME, "")
-    stripped_existing_baggage = Baggage.strip_sentry_baggage(existing_baggage)
-
-    separator = "," if len(stripped_existing_baggage) > 0 else ""
-
-    headers[BAGGAGE_HEADER_NAME] = (
-        stripped_existing_baggage + separator + sentry_baggage
-    )
diff --git a/sentry_sdk/integrations/huggingface_hub.py b/sentry_sdk/integrations/huggingface_hub.py
index 39a667dde9..8509cadefa 100644
--- a/sentry_sdk/integrations/huggingface_hub.py
+++ b/sentry_sdk/integrations/huggingface_hub.py
@@ -1,3 +1,4 @@
+import sys
 import inspect
 from functools import wraps
 
@@ -11,6 +12,7 @@
 from sentry_sdk.utils import (
     capture_internal_exceptions,
     event_from_exception,
+    reraise,
 )
 
 from typing import TYPE_CHECKING
@@ -126,9 +128,11 @@ def new_huggingface_task(*args: "Any", **kwargs: "Any") -> "Any":
         try:
             res = f(*args, **kwargs)
         except Exception as e:
-            _capture_exception(e)
-            span.__exit__(None, None, None)
-            raise e from None
+            exc_info = sys.exc_info()
+            with capture_internal_exceptions():
+                _capture_exception(e)
+                span.__exit__(None, None, None)
+            reraise(*exc_info)
 
         # Output attributes
         finish_reason = None
diff --git a/sentry_sdk/integrations/langchain.py b/sentry_sdk/integrations/langchain.py
index 950f437d4c..7a5e863e4d 100644
--- a/sentry_sdk/integrations/langchain.py
+++ b/sentry_sdk/integrations/langchain.py
@@ -1,6 +1,7 @@
 import contextvars
 import itertools
 import sys
+import json
 import warnings
 from collections import OrderedDict
 from functools import wraps
@@ -14,6 +15,7 @@
     normalize_message_roles,
     set_data_normalized,
     truncate_and_annotate_messages,
+    transform_content_part,
 )
 from sentry_sdk.consts import OP, SPANDATA
 from sentry_sdk.integrations import DidNotEnable, Integration
@@ -35,6 +37,7 @@
     from uuid import UUID
 
     from sentry_sdk.tracing import Span
+    from sentry_sdk._types import TextPart
 
 
 try:
@@ -117,6 +120,39 @@
 }
 
 
+def _transform_langchain_content_block(
+    content_block: "Dict[str, Any]",
+) -> "Dict[str, Any]":
+    """
+    Transform a LangChain content block using the shared transform_content_part function.
+
+    Returns the original content block if transformation is not applicable
+    (e.g., for text blocks or unrecognized formats).
+    """
+    result = transform_content_part(content_block)
+    return result if result is not None else content_block
+
+
+def _transform_langchain_message_content(content: "Any") -> "Any":
+    """
+    Transform LangChain message content, handling both string content and
+    list of content blocks.
+    """
+    if isinstance(content, str):
+        return content
+
+    if isinstance(content, (list, tuple)):
+        transformed = []
+        for block in content:
+            if isinstance(block, dict):
+                transformed.append(_transform_langchain_content_block(block))
+            else:
+                transformed.append(block)
+        return transformed
+
+    return content
+
+
 # Contextvar to track agent names in a stack for re-entrant agent support
 _agent_stack: "contextvars.ContextVar[Optional[List[Optional[str]]]]" = (
     contextvars.ContextVar("langchain_agent_stack", default=None)
@@ -155,6 +191,40 @@ def _get_current_agent() -> "Optional[str]":
     return None
 
 
+def _get_system_instructions(messages: "List[List[BaseMessage]]") -> "List[str]":
+    system_instructions = []
+
+    for list_ in messages:
+        for message in list_:
+            # type of content: str | list[str | dict] | None
+            if message.type == "system" and isinstance(message.content, str):
+                system_instructions.append(message.content)
+
+            elif message.type == "system" and isinstance(message.content, list):
+                for item in message.content:
+                    if isinstance(item, str):
+                        system_instructions.append(item)
+
+                    elif isinstance(item, dict) and item.get("type") == "text":
+                        instruction = item.get("text")
+                        if isinstance(instruction, str):
+                            system_instructions.append(instruction)
+
+    return system_instructions
+
+
+def _transform_system_instructions(
+    system_instructions: "List[str]",
+) -> "List[TextPart]":
+    return [
+        {
+            "type": "text",
+            "content": instruction,
+        }
+        for instruction in system_instructions
+    ]
+
+
 class LangchainIntegration(Integration):
     identifier = "langchain"
     origin = f"auto.ai.{identifier}"
@@ -234,7 +304,9 @@ def _handle_error(self, run_id: "UUID", error: "Any") -> None:
             del self.span_map[run_id]
 
     def _normalize_langchain_message(self, message: "BaseMessage") -> "Any":
-        parsed = {"role": message.type, "content": message.content}
+        # Transform content to handle multimodal data (images, audio, video, files)
+        transformed_content = _transform_langchain_message_content(message.content)
+        parsed = {"role": message.type, "content": transformed_content}
         parsed.update(message.additional_kwargs)
         return parsed
 
@@ -394,9 +466,19 @@ def on_chat_model_start(
             _set_tools_on_span(span, all_params.get("tools"))
 
             if should_send_default_pii() and self.include_prompts:
+                system_instructions = _get_system_instructions(messages)
+                if len(system_instructions) > 0:
+                    span.set_data(
+                        SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS,
+                        json.dumps(_transform_system_instructions(system_instructions)),
+                    )
+
                 normalized_messages = []
                 for list_ in messages:
                     for message in list_:
+                        if message.type == "system":
+                            continue
+
                         normalized_messages.append(
                             self._normalize_langchain_message(message)
                         )
diff --git a/sentry_sdk/integrations/litellm.py b/sentry_sdk/integrations/litellm.py
index 08cb217962..28bcc34d3e 100644
--- a/sentry_sdk/integrations/litellm.py
+++ b/sentry_sdk/integrations/litellm.py
@@ -1,3 +1,4 @@
+import copy
 from typing import TYPE_CHECKING
 
 import sentry_sdk
@@ -7,6 +8,8 @@
     get_start_span_function,
     set_data_normalized,
     truncate_and_annotate_messages,
+    transform_openai_content_part,
+    truncate_and_annotate_embedding_inputs,
 )
 from sentry_sdk.consts import SPANDATA
 from sentry_sdk.integrations import DidNotEnable, Integration
@@ -14,11 +17,12 @@
 from sentry_sdk.utils import event_from_exception
 
 if TYPE_CHECKING:
-    from typing import Any, Dict
+    from typing import Any, Dict, List
     from datetime import datetime
 
 try:
     import litellm  # type: ignore[import-not-found]
+    from litellm import input_callback, success_callback, failure_callback
 except ImportError:
     raise DidNotEnable("LiteLLM not installed")
 
@@ -35,6 +39,33 @@ def _get_metadata_dict(kwargs: "Dict[str, Any]") -> "Dict[str, Any]":
     return metadata
 
 
+def _convert_message_parts(messages: "List[Dict[str, Any]]") -> "List[Dict[str, Any]]":
+    """
+    Convert the message parts from OpenAI format to the `gen_ai.request.messages` format
+    using the OpenAI-specific transformer (LiteLLM uses OpenAI's message format).
+
+    Deep copies messages to avoid mutating original kwargs.
+    """
+    # Deep copy to avoid mutating original messages from kwargs
+    messages = copy.deepcopy(messages)
+
+    for message in messages:
+        if not isinstance(message, dict):
+            continue
+        content = message.get("content")
+        if isinstance(content, (list, tuple)):
+            transformed = []
+            for item in content:
+                if isinstance(item, dict):
+                    result = transform_openai_content_part(item)
+                    # If transformation succeeded, use the result; otherwise keep original
+                    transformed.append(result if result is not None else item)
+                else:
+                    transformed.append(item)
+            message["content"] = transformed
+    return messages
+
+
 def _input_callback(kwargs: "Dict[str, Any]") -> None:
     """Handle the start of a request."""
     integration = sentry_sdk.get_client().get_integration(LiteLLMIntegration)
@@ -88,7 +119,9 @@ def _input_callback(kwargs: "Dict[str, Any]") -> None:
                     if isinstance(embedding_input, list)
                     else [embedding_input]
                 )
-                messages_data = truncate_and_annotate_messages(input_list, span, scope)
+                messages_data = truncate_and_annotate_embedding_inputs(
+                    input_list, span, scope
+                )
                 if messages_data is not None:
                     set_data_normalized(
                         span,
@@ -101,6 +134,7 @@ def _input_callback(kwargs: "Dict[str, Any]") -> None:
             messages = kwargs.get("messages", [])
             if messages:
                 scope = sentry_sdk.get_current_scope()
+                messages = _convert_message_parts(messages)
                 messages_data = truncate_and_annotate_messages(messages, span, scope)
                 if messages_data is not None:
                     set_data_normalized(
@@ -278,14 +312,14 @@ def __init__(self: "LiteLLMIntegration", include_prompts: bool = True) -> None:
     @staticmethod
     def setup_once() -> None:
         """Set up LiteLLM callbacks for monitoring."""
-        litellm.input_callback = litellm.input_callback or []
+        litellm.input_callback = input_callback or []
         if _input_callback not in litellm.input_callback:
             litellm.input_callback.append(_input_callback)
 
-        litellm.success_callback = litellm.success_callback or []
+        litellm.success_callback = success_callback or []
         if _success_callback not in litellm.success_callback:
             litellm.success_callback.append(_success_callback)
 
-        litellm.failure_callback = litellm.failure_callback or []
+        litellm.failure_callback = failure_callback or []
         if _failure_callback not in litellm.failure_callback:
             litellm.failure_callback.append(_failure_callback)
diff --git a/sentry_sdk/integrations/openai.py b/sentry_sdk/integrations/openai.py
index 53d464c3c4..081744bfd5 100644
--- a/sentry_sdk/integrations/openai.py
+++ b/sentry_sdk/integrations/openai.py
@@ -1,4 +1,8 @@
+import sys
+import json
+import time
 from functools import wraps
+from collections.abc import Iterable
 
 import sentry_sdk
 from sentry_sdk import consts
@@ -7,6 +11,16 @@
     set_data_normalized,
     normalize_message_roles,
     truncate_and_annotate_messages,
+    truncate_and_annotate_embedding_inputs,
+)
+from sentry_sdk.ai._openai_completions_api import (
+    _is_system_instruction as _is_system_instruction_completions,
+    _get_system_instructions as _get_system_instructions_completions,
+    _transform_system_instructions,
+)
+from sentry_sdk.ai._openai_responses_api import (
+    _is_system_instruction as _is_system_instruction_responses,
+    _get_system_instructions as _get_system_instructions_responses,
 )
 from sentry_sdk.consts import SPANDATA
 from sentry_sdk.integrations import DidNotEnable, Integration
@@ -16,13 +30,27 @@
     capture_internal_exceptions,
     event_from_exception,
     safe_serialize,
+    reraise,
 )
 
 from typing import TYPE_CHECKING
 
 if TYPE_CHECKING:
-    from typing import Any, Iterable, List, Optional, Callable, AsyncIterator, Iterator
+    from typing import (
+        Any,
+        List,
+        Optional,
+        Callable,
+        AsyncIterator,
+        Iterator,
+        Union,
+        Iterable,
+    )
     from sentry_sdk.tracing import Span
+    from sentry_sdk._types import TextPart
+
+    from openai.types.responses import ResponseInputParam
+    from openai import Omit
 
 try:
     try:
@@ -39,7 +67,11 @@
     from openai.resources import Embeddings, AsyncEmbeddings
 
     if TYPE_CHECKING:
-        from openai.types.chat import ChatCompletionMessageParam, ChatCompletionChunk
+        from openai.types.chat import (
+            ChatCompletionMessageParam,
+            ChatCompletionChunk,
+            ChatCompletionSystemMessageParam,
+        )
 except ImportError:
     raise DidNotEnable("OpenAI not installed")
 
@@ -84,9 +116,12 @@ def setup_once() -> None:
             AsyncResponses.create = _wrap_async_responses_create(AsyncResponses.create)
 
     def count_tokens(self: "OpenAIIntegration", s: str) -> int:
-        if self.tiktoken_encoding is not None:
+        if self.tiktoken_encoding is None:
+            return 0
+        try:
             return len(self.tiktoken_encoding.encode_ordinary(s))
-        return 0
+        except Exception:
+            return 0
 
 
 def _capture_exception(exc: "Any", manual_span_cleanup: bool = True) -> None:
@@ -157,8 +192,8 @@ def _calculate_token_usage(
                 output_tokens += count_tokens(message)
         elif hasattr(response, "choices"):
             for choice in response.choices:
-                if hasattr(choice, "message"):
-                    output_tokens += count_tokens(choice.message)
+                if hasattr(choice, "message") and hasattr(choice.message, "content"):
+                    output_tokens += count_tokens(choice.message.content)
 
     # Do not set token data if it is 0
     input_tokens = input_tokens or None
@@ -177,12 +212,9 @@ def _calculate_token_usage(
     )
 
 
-def _set_input_data(
-    span: "Span",
+def _get_input_messages(
     kwargs: "dict[str, Any]",
-    operation: str,
-    integration: "OpenAIIntegration",
-) -> None:
+) -> "Optional[Union[Iterable[Any], list[str]]]":
     # Input messages (the prompt or data sent to the model)
     messages = kwargs.get("messages")
     if messages is None:
@@ -191,29 +223,15 @@ def _set_input_data(
     if isinstance(messages, str):
         messages = [messages]
 
-    if (
-        messages is not None
-        and len(messages) > 0
-        and should_send_default_pii()
-        and integration.include_prompts
-    ):
-        normalized_messages = normalize_message_roles(messages)
-        scope = sentry_sdk.get_current_scope()
-        messages_data = truncate_and_annotate_messages(normalized_messages, span, scope)
-        if messages_data is not None:
-            # Use appropriate field based on operation type
-            if operation == "embeddings":
-                set_data_normalized(
-                    span, SPANDATA.GEN_AI_EMBEDDINGS_INPUT, messages_data, unpack=False
-                )
-            else:
-                set_data_normalized(
-                    span, SPANDATA.GEN_AI_REQUEST_MESSAGES, messages_data, unpack=False
-                )
+    return messages
+
 
+def _commmon_set_input_data(
+    span: "Span",
+    kwargs: "dict[str, Any]",
+) -> None:
     # Input attributes: Common
     set_data_normalized(span, SPANDATA.GEN_AI_SYSTEM, "openai")
-    set_data_normalized(span, SPANDATA.GEN_AI_OPERATION_NAME, operation)
 
     # Input attributes: Optional
     kwargs_keys_to_attributes = {
@@ -239,11 +257,182 @@ def _set_input_data(
         )
 
 
+def _set_responses_api_input_data(
+    span: "Span",
+    kwargs: "dict[str, Any]",
+    integration: "OpenAIIntegration",
+) -> None:
+    explicit_instructions: "Union[Optional[str], Omit]" = kwargs.get("instructions")
+    messages: "Optional[Union[str, ResponseInputParam]]" = kwargs.get("input")
+
+    if not should_send_default_pii() or not integration.include_prompts:
+        set_data_normalized(span, SPANDATA.GEN_AI_OPERATION_NAME, "responses")
+        _commmon_set_input_data(span, kwargs)
+        return
+
+    if (
+        messages is None
+        and explicit_instructions is not None
+        and _is_given(explicit_instructions)
+    ):
+        span.set_data(
+            SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS,
+            json.dumps(
+                [
+                    {
+                        "type": "text",
+                        "content": explicit_instructions,
+                    }
+                ]
+            ),
+        )
+
+        set_data_normalized(span, SPANDATA.GEN_AI_OPERATION_NAME, "responses")
+        _commmon_set_input_data(span, kwargs)
+        return
+
+    if messages is None:
+        set_data_normalized(span, SPANDATA.GEN_AI_OPERATION_NAME, "responses")
+        _commmon_set_input_data(span, kwargs)
+        return
+
+    instructions_text_parts: "list[TextPart]" = []
+    if explicit_instructions is not None and _is_given(explicit_instructions):
+        instructions_text_parts.append(
+            {
+                "type": "text",
+                "content": explicit_instructions,
+            }
+        )
+
+    system_instructions = _get_system_instructions_responses(messages)
+    # Deliberate use of function accepting completions API type because
+    # of shared structure FOR THIS PURPOSE ONLY.
+    instructions_text_parts += _transform_system_instructions(system_instructions)
+
+    if len(instructions_text_parts) > 0:
+        span.set_data(
+            SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS,
+            json.dumps(instructions_text_parts),
+        )
+
+    if isinstance(messages, str):
+        normalized_messages = normalize_message_roles([messages])  # type: ignore
+        scope = sentry_sdk.get_current_scope()
+        messages_data = truncate_and_annotate_messages(normalized_messages, span, scope)
+        if messages_data is not None:
+            set_data_normalized(
+                span, SPANDATA.GEN_AI_REQUEST_MESSAGES, messages_data, unpack=False
+            )
+
+        set_data_normalized(span, SPANDATA.GEN_AI_OPERATION_NAME, "responses")
+        _commmon_set_input_data(span, kwargs)
+        return
+
+    non_system_messages = [
+        message for message in messages if not _is_system_instruction_responses(message)
+    ]
+    if len(non_system_messages) > 0:
+        normalized_messages = normalize_message_roles(non_system_messages)
+        scope = sentry_sdk.get_current_scope()
+        messages_data = truncate_and_annotate_messages(normalized_messages, span, scope)
+        if messages_data is not None:
+            set_data_normalized(
+                span, SPANDATA.GEN_AI_REQUEST_MESSAGES, messages_data, unpack=False
+            )
+
+    set_data_normalized(span, SPANDATA.GEN_AI_OPERATION_NAME, "responses")
+    _commmon_set_input_data(span, kwargs)
+
+
+def _set_completions_api_input_data(
+    span: "Span",
+    kwargs: "dict[str, Any]",
+    integration: "OpenAIIntegration",
+) -> None:
+    messages: "Optional[Union[str, Iterable[ChatCompletionMessageParam]]]" = kwargs.get(
+        "messages"
+    )
+
+    if (
+        not should_send_default_pii()
+        or not integration.include_prompts
+        or messages is None
+    ):
+        set_data_normalized(span, SPANDATA.GEN_AI_OPERATION_NAME, "chat")
+        _commmon_set_input_data(span, kwargs)
+        return
+
+    system_instructions = _get_system_instructions_completions(messages)
+    if len(system_instructions) > 0:
+        span.set_data(
+            SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS,
+            json.dumps(_transform_system_instructions(system_instructions)),
+        )
+
+    if isinstance(messages, str):
+        normalized_messages = normalize_message_roles([messages])  # type: ignore
+        scope = sentry_sdk.get_current_scope()
+        messages_data = truncate_and_annotate_messages(normalized_messages, span, scope)
+        if messages_data is not None:
+            set_data_normalized(
+                span, SPANDATA.GEN_AI_REQUEST_MESSAGES, messages_data, unpack=False
+            )
+        set_data_normalized(span, SPANDATA.GEN_AI_OPERATION_NAME, "chat")
+        _commmon_set_input_data(span, kwargs)
+        return
+
+    non_system_messages = [
+        message
+        for message in messages
+        if not _is_system_instruction_completions(message)
+    ]
+    if len(non_system_messages) > 0:
+        normalized_messages = normalize_message_roles(non_system_messages)  # type: ignore
+        scope = sentry_sdk.get_current_scope()
+        messages_data = truncate_and_annotate_messages(normalized_messages, span, scope)
+        if messages_data is not None:
+            set_data_normalized(
+                span, SPANDATA.GEN_AI_REQUEST_MESSAGES, messages_data, unpack=False
+            )
+
+    set_data_normalized(span, SPANDATA.GEN_AI_OPERATION_NAME, "chat")
+    _commmon_set_input_data(span, kwargs)
+
+
+def _set_embeddings_input_data(
+    span: "Span",
+    kwargs: "dict[str, Any]",
+    integration: "OpenAIIntegration",
+) -> None:
+    messages = _get_input_messages(kwargs)
+
+    if (
+        messages is not None
+        and len(messages) > 0  # type: ignore
+        and should_send_default_pii()
+        and integration.include_prompts
+    ):
+        normalized_messages = normalize_message_roles(messages)  # type: ignore
+        scope = sentry_sdk.get_current_scope()
+        messages_data = truncate_and_annotate_embedding_inputs(
+            normalized_messages, span, scope
+        )
+        if messages_data is not None:
+            set_data_normalized(
+                span, SPANDATA.GEN_AI_EMBEDDINGS_INPUT, messages_data, unpack=False
+            )
+
+    set_data_normalized(span, SPANDATA.GEN_AI_OPERATION_NAME, "embeddings")
+    _commmon_set_input_data(span, kwargs)
+
+
 def _set_output_data(
     span: "Span",
     response: "Any",
     kwargs: "dict[str, Any]",
     integration: "OpenAIIntegration",
+    start_time: "Optional[float]" = None,
     finish_span: bool = True,
 ) -> None:
     if hasattr(response, "model"):
@@ -258,6 +447,8 @@ def _set_output_data(
     if messages is not None and isinstance(messages, str):
         messages = [messages]
 
+    ttft: "Optional[float]" = None
+
     if hasattr(response, "choices"):
         if should_send_default_pii() and integration.include_prompts:
             response_text = [
@@ -315,6 +506,7 @@ def _set_output_data(
         old_iterator = response._iterator
 
         def new_iterator() -> "Iterator[ChatCompletionChunk]":
+            nonlocal ttft
             count_tokens_manually = True
             for x in old_iterator:
                 with capture_internal_exceptions():
@@ -325,6 +517,8 @@ def new_iterator() -> "Iterator[ChatCompletionChunk]":
                             if hasattr(choice, "delta") and hasattr(
                                 choice.delta, "content"
                             ):
+                                if start_time is not None and ttft is None:
+                                    ttft = time.perf_counter() - start_time
                                 content = choice.delta.content
                                 if len(data_buf) <= choice_index:
                                     data_buf.append([])
@@ -333,6 +527,8 @@ def new_iterator() -> "Iterator[ChatCompletionChunk]":
 
                     # OpenAI responses API
                     elif hasattr(x, "delta"):
+                        if start_time is not None and ttft is None:
+                            ttft = time.perf_counter() - start_time
                         if len(data_buf) == 0:
                             data_buf.append([])
                         data_buf[0].append(x.delta or "")
@@ -351,6 +547,10 @@ def new_iterator() -> "Iterator[ChatCompletionChunk]":
                 yield x
 
             with capture_internal_exceptions():
+                if ttft is not None:
+                    set_data_normalized(
+                        span, SPANDATA.GEN_AI_RESPONSE_TIME_TO_FIRST_TOKEN, ttft
+                    )
                 if len(data_buf) > 0:
                     all_responses = ["".join(chunk) for chunk in data_buf]
                     if should_send_default_pii() and integration.include_prompts:
@@ -370,6 +570,7 @@ def new_iterator() -> "Iterator[ChatCompletionChunk]":
                 span.__exit__(None, None, None)
 
         async def new_iterator_async() -> "AsyncIterator[ChatCompletionChunk]":
+            nonlocal ttft
             count_tokens_manually = True
             async for x in old_iterator:
                 with capture_internal_exceptions():
@@ -380,6 +581,8 @@ async def new_iterator_async() -> "AsyncIterator[ChatCompletionChunk]":
                             if hasattr(choice, "delta") and hasattr(
                                 choice.delta, "content"
                             ):
+                                if start_time is not None and ttft is None:
+                                    ttft = time.perf_counter() - start_time
                                 content = choice.delta.content
                                 if len(data_buf) <= choice_index:
                                     data_buf.append([])
@@ -388,6 +591,8 @@ async def new_iterator_async() -> "AsyncIterator[ChatCompletionChunk]":
 
                     # OpenAI responses API
                     elif hasattr(x, "delta"):
+                        if start_time is not None and ttft is None:
+                            ttft = time.perf_counter() - start_time
                         if len(data_buf) == 0:
                             data_buf.append([])
                         data_buf[0].append(x.delta or "")
@@ -406,6 +611,10 @@ async def new_iterator_async() -> "AsyncIterator[ChatCompletionChunk]":
                 yield x
 
             with capture_internal_exceptions():
+                if ttft is not None:
+                    set_data_normalized(
+                        span, SPANDATA.GEN_AI_RESPONSE_TIME_TO_FIRST_TOKEN, ttft
+                    )
                 if len(data_buf) > 0:
                     all_responses = ["".join(chunk) for chunk in data_buf]
                     if should_send_default_pii() and integration.include_prompts:
@@ -449,20 +658,20 @@ def _new_chat_completion_common(f: "Any", *args: "Any", **kwargs: "Any") -> "Any
         return f(*args, **kwargs)
 
     model = kwargs.get("model")
-    operation = "chat"
 
     span = sentry_sdk.start_span(
         op=consts.OP.GEN_AI_CHAT,
-        name=f"{operation} {model}",
+        name=f"chat {model}",
         origin=OpenAIIntegration.origin,
     )
     span.__enter__()
 
-    _set_input_data(span, kwargs, operation, integration)
+    _set_completions_api_input_data(span, kwargs, integration)
 
+    start_time = time.perf_counter()
     response = yield f, args, kwargs
 
-    _set_output_data(span, response, kwargs, integration, finish_span=True)
+    _set_output_data(span, response, kwargs, integration, start_time, finish_span=True)
 
     return response
 
@@ -480,8 +689,10 @@ def _execute_sync(f: "Any", *args: "Any", **kwargs: "Any") -> "Any":
             try:
                 result = f(*args, **kwargs)
             except Exception as e:
-                _capture_exception(e)
-                raise e from None
+                exc_info = sys.exc_info()
+                with capture_internal_exceptions():
+                    _capture_exception(e)
+                reraise(*exc_info)
 
             return gen.send(result)
         except StopIteration as e:
@@ -512,8 +723,10 @@ async def _execute_async(f: "Any", *args: "Any", **kwargs: "Any") -> "Any":
             try:
                 result = await f(*args, **kwargs)
             except Exception as e:
-                _capture_exception(e)
-                raise e from None
+                exc_info = sys.exc_info()
+                with capture_internal_exceptions():
+                    _capture_exception(e)
+                reraise(*exc_info)
 
             return gen.send(result)
         except StopIteration as e:
@@ -537,14 +750,13 @@ def _new_embeddings_create_common(f: "Any", *args: "Any", **kwargs: "Any") -> "A
         return f(*args, **kwargs)
 
     model = kwargs.get("model")
-    operation = "embeddings"
 
     with sentry_sdk.start_span(
         op=consts.OP.GEN_AI_EMBEDDINGS,
-        name=f"{operation} {model}",
+        name=f"embeddings {model}",
         origin=OpenAIIntegration.origin,
     ) as span:
-        _set_input_data(span, kwargs, operation, integration)
+        _set_embeddings_input_data(span, kwargs, integration)
 
         response = yield f, args, kwargs
 
@@ -566,8 +778,10 @@ def _execute_sync(f: "Any", *args: "Any", **kwargs: "Any") -> "Any":
             try:
                 result = f(*args, **kwargs)
             except Exception as e:
-                _capture_exception(e, manual_span_cleanup=False)
-                raise e from None
+                exc_info = sys.exc_info()
+                with capture_internal_exceptions():
+                    _capture_exception(e, manual_span_cleanup=False)
+                reraise(*exc_info)
 
             return gen.send(result)
         except StopIteration as e:
@@ -597,8 +811,10 @@ async def _execute_async(f: "Any", *args: "Any", **kwargs: "Any") -> "Any":
             try:
                 result = await f(*args, **kwargs)
             except Exception as e:
-                _capture_exception(e, manual_span_cleanup=False)
-                raise e from None
+                exc_info = sys.exc_info()
+                with capture_internal_exceptions():
+                    _capture_exception(e, manual_span_cleanup=False)
+                reraise(*exc_info)
 
             return gen.send(result)
         except StopIteration as e:
@@ -621,20 +837,20 @@ def _new_responses_create_common(f: "Any", *args: "Any", **kwargs: "Any") -> "An
         return f(*args, **kwargs)
 
     model = kwargs.get("model")
-    operation = "responses"
 
     span = sentry_sdk.start_span(
         op=consts.OP.GEN_AI_RESPONSES,
-        name=f"{operation} {model}",
+        name=f"responses {model}",
         origin=OpenAIIntegration.origin,
     )
     span.__enter__()
 
-    _set_input_data(span, kwargs, operation, integration)
+    _set_responses_api_input_data(span, kwargs, integration)
 
+    start_time = time.perf_counter()
     response = yield f, args, kwargs
 
-    _set_output_data(span, response, kwargs, integration, finish_span=True)
+    _set_output_data(span, response, kwargs, integration, start_time, finish_span=True)
 
     return response
 
@@ -652,8 +868,10 @@ def _execute_sync(f: "Any", *args: "Any", **kwargs: "Any") -> "Any":
             try:
                 result = f(*args, **kwargs)
             except Exception as e:
-                _capture_exception(e)
-                raise e from None
+                exc_info = sys.exc_info()
+                with capture_internal_exceptions():
+                    _capture_exception(e)
+                reraise(*exc_info)
 
             return gen.send(result)
         except StopIteration as e:
@@ -683,8 +901,10 @@ async def _execute_async(f: "Any", *args: "Any", **kwargs: "Any") -> "Any":
             try:
                 result = await f(*args, **kwargs)
             except Exception as e:
-                _capture_exception(e)
-                raise e from None
+                exc_info = sys.exc_info()
+                with capture_internal_exceptions():
+                    _capture_exception(e)
+                reraise(*exc_info)
 
             return gen.send(result)
         except StopIteration as e:
diff --git a/sentry_sdk/integrations/openai_agents/__init__.py b/sentry_sdk/integrations/openai_agents/__init__.py
index 3ad7d2ee8d..deb136de01 100644
--- a/sentry_sdk/integrations/openai_agents/__init__.py
+++ b/sentry_sdk/integrations/openai_agents/__init__.py
@@ -4,13 +4,14 @@
     _create_get_model_wrapper,
     _create_get_all_tools_wrapper,
     _create_run_wrapper,
+    _create_run_streamed_wrapper,
     _patch_agent_run,
     _patch_error_tracing,
 )
 
 try:
     # "agents" is too generic. If someone has an agents.py file in their project
-    # or another package that's importable via "agents", no ImportError would not
+    # or another package that's importable via "agents", no ImportError would
     # be thrown and the integration would enable itself even if openai-agents is
     # not installed. That's why we're adding the second, more specific import
     # after it, even if we don't use it.
@@ -25,12 +26,16 @@ def _patch_runner() -> None:
     # Create the root span for one full agent run (including eventual handoffs)
     # Note agents.run.DEFAULT_AGENT_RUNNER.run_sync is a wrapper around
     # agents.run.DEFAULT_AGENT_RUNNER.run. It does not need to be wrapped separately.
-    # TODO-anton: Also patch streaming runner: agents.Runner.run_streamed
     agents.run.DEFAULT_AGENT_RUNNER.run = _create_run_wrapper(
         agents.run.DEFAULT_AGENT_RUNNER.run
     )
 
-    # Creating the actual spans for each agent run.
+    # Patch streaming runner
+    agents.run.DEFAULT_AGENT_RUNNER.run_streamed = _create_run_streamed_wrapper(
+        agents.run.DEFAULT_AGENT_RUNNER.run_streamed
+    )
+
+    # Creating the actual spans for each agent run (works for both streaming and non-streaming).
     _patch_agent_run()
 
 
diff --git a/sentry_sdk/integrations/openai_agents/patches/__init__.py b/sentry_sdk/integrations/openai_agents/patches/__init__.py
index 33058f01a1..b53ca79e19 100644
--- a/sentry_sdk/integrations/openai_agents/patches/__init__.py
+++ b/sentry_sdk/integrations/openai_agents/patches/__init__.py
@@ -1,5 +1,5 @@
 from .models import _create_get_model_wrapper  # noqa: F401
 from .tools import _create_get_all_tools_wrapper  # noqa: F401
-from .runner import _create_run_wrapper  # noqa: F401
+from .runner import _create_run_wrapper, _create_run_streamed_wrapper  # noqa: F401
 from .agent_run import _patch_agent_run  # noqa: F401
 from .error_tracing import _patch_error_tracing  # noqa: F401
diff --git a/sentry_sdk/integrations/openai_agents/patches/agent_run.py b/sentry_sdk/integrations/openai_agents/patches/agent_run.py
index 29649af945..eeb821d42a 100644
--- a/sentry_sdk/integrations/openai_agents/patches/agent_run.py
+++ b/sentry_sdk/integrations/openai_agents/patches/agent_run.py
@@ -1,8 +1,9 @@
 import sys
 from functools import wraps
 
+from sentry_sdk.consts import SPANDATA
 from sentry_sdk.integrations import DidNotEnable
-from sentry_sdk.utils import reraise
+from sentry_sdk.utils import capture_internal_exceptions, reraise
 from ..spans import (
     invoke_agent_span,
     end_invoke_agent_span,
@@ -31,22 +32,10 @@ def _patch_agent_run() -> None:
 
     # Store original methods
     original_run_single_turn = agents.run.AgentRunner._run_single_turn
+    original_run_single_turn_streamed = agents.run.AgentRunner._run_single_turn_streamed
     original_execute_handoffs = agents._run_impl.RunImpl.execute_handoffs
     original_execute_final_output = agents._run_impl.RunImpl.execute_final_output
 
-    def _start_invoke_agent_span(
-        context_wrapper: "agents.RunContextWrapper",
-        agent: "agents.Agent",
-        kwargs: "dict[str, Any]",
-    ) -> "Span":
-        """Start an agent invocation span"""
-        # Store the agent on the context wrapper so we can access it later
-        context_wrapper._sentry_current_agent = agent
-        span = invoke_agent_span(context_wrapper, agent, kwargs)
-        context_wrapper._sentry_agent_span = span
-
-        return span
-
     def _has_active_agent_span(context_wrapper: "agents.RunContextWrapper") -> bool:
         """Check if there's an active agent span for this context"""
         return getattr(context_wrapper, "_sentry_current_agent", None) is not None
@@ -57,6 +46,46 @@ def _get_current_agent(
         """Get the current agent from context wrapper"""
         return getattr(context_wrapper, "_sentry_current_agent", None)
 
+    def _close_streaming_workflow_span(agent: "Optional[agents.Agent]") -> None:
+        """Close the workflow span for streaming executions if it exists."""
+        if agent and hasattr(agent, "_sentry_workflow_span"):
+            workflow_span = agent._sentry_workflow_span
+            workflow_span.__exit__(*sys.exc_info())
+            delattr(agent, "_sentry_workflow_span")
+
+    def _maybe_start_agent_span(
+        context_wrapper: "agents.RunContextWrapper",
+        agent: "agents.Agent",
+        should_run_agent_start_hooks: bool,
+        span_kwargs: "dict[str, Any]",
+        is_streaming: bool = False,
+    ) -> "Optional[Span]":
+        """
+        Start an agent invocation span if conditions are met.
+        Handles ending any existing span for a different agent.
+
+        Returns the new span if started, or the existing span if conditions aren't met.
+        """
+        if not (should_run_agent_start_hooks and agent and context_wrapper):
+            return getattr(context_wrapper, "_sentry_agent_span", None)
+
+        # End any existing span for a different agent
+        if _has_active_agent_span(context_wrapper):
+            current_agent = _get_current_agent(context_wrapper)
+            if current_agent and current_agent != agent:
+                end_invoke_agent_span(context_wrapper, current_agent)
+
+        # Store the agent on the context wrapper so we can access it later
+        context_wrapper._sentry_current_agent = agent
+        span = invoke_agent_span(context_wrapper, agent, span_kwargs)
+        context_wrapper._sentry_agent_span = span
+        agent._sentry_agent_span = span
+
+        if is_streaming:
+            span.set_data(SPANDATA.GEN_AI_RESPONSE_STREAMING, True)
+
+        return span
+
     @wraps(
         original_run_single_turn.__func__
         if hasattr(original_run_single_turn, "__func__")
@@ -68,28 +97,18 @@ async def patched_run_single_turn(
         """Patched _run_single_turn that creates agent invocation spans"""
         agent = kwargs.get("agent")
         context_wrapper = kwargs.get("context_wrapper")
-        should_run_agent_start_hooks = kwargs.get("should_run_agent_start_hooks")
-
-        span = getattr(context_wrapper, "_sentry_agent_span", None)
-        # Start agent span when agent starts (but only once per agent)
-        if should_run_agent_start_hooks and agent and context_wrapper:
-            # End any existing span for a different agent
-            if _has_active_agent_span(context_wrapper):
-                current_agent = _get_current_agent(context_wrapper)
-                if current_agent and current_agent != agent:
-                    end_invoke_agent_span(context_wrapper, current_agent)
+        should_run_agent_start_hooks = kwargs.get("should_run_agent_start_hooks", False)
 
-            span = _start_invoke_agent_span(context_wrapper, agent, kwargs)
-            agent._sentry_agent_span = span
+        span = _maybe_start_agent_span(
+            context_wrapper, agent, should_run_agent_start_hooks, kwargs
+        )
 
-        # Call original method with all the correct parameters
         try:
             result = await original_run_single_turn(*args, **kwargs)
         except Exception as exc:
             if span is not None and span.timestamp is None:
                 _record_exception_on_span(span, exc)
                 end_invoke_agent_span(context_wrapper, agent)
-
             reraise(*sys.exc_info())
 
         return result
@@ -117,7 +136,11 @@ async def patched_execute_handoffs(
         # Call original method with all parameters
         try:
             result = await original_execute_handoffs(*args, **kwargs)
-
+        except Exception:
+            exc_info = sys.exc_info()
+            with capture_internal_exceptions():
+                _close_streaming_workflow_span(agent)
+            reraise(*exc_info)
         finally:
             # End span for current agent after handoff processing is complete
             if agent and context_wrapper and _has_active_agent_span(context_wrapper):
@@ -139,18 +162,84 @@ async def patched_execute_final_output(
         context_wrapper = kwargs.get("context_wrapper")
         final_output = kwargs.get("final_output")
 
-        # Call original method with all parameters
         try:
             result = await original_execute_final_output(*args, **kwargs)
         finally:
-            # End span for current agent after final output processing is complete
-            if agent and context_wrapper and _has_active_agent_span(context_wrapper):
-                end_invoke_agent_span(context_wrapper, agent, final_output)
+            with capture_internal_exceptions():
+                if (
+                    agent
+                    and context_wrapper
+                    and _has_active_agent_span(context_wrapper)
+                ):
+                    end_invoke_agent_span(context_wrapper, agent, final_output)
+                # For streaming, close the workflow span (non-streaming uses context manager in _create_run_wrapper)
+                _close_streaming_workflow_span(agent)
+
+        return result
+
+    @wraps(
+        original_run_single_turn_streamed.__func__
+        if hasattr(original_run_single_turn_streamed, "__func__")
+        else original_run_single_turn_streamed
+    )
+    async def patched_run_single_turn_streamed(
+        cls: "agents.Runner", *args: "Any", **kwargs: "Any"
+    ) -> "Any":
+        """Patched _run_single_turn_streamed that creates agent invocation spans for streaming.
+
+        Note: Unlike _run_single_turn which uses keyword-only arguments (*,),
+        _run_single_turn_streamed uses positional arguments. The call signature is:
+        _run_single_turn_streamed(
+            streamed_result,              # args[0]
+            agent,                        # args[1]
+            hooks,                        # args[2]
+            context_wrapper,              # args[3]
+            run_config,                   # args[4]
+            should_run_agent_start_hooks, # args[5]
+            tool_use_tracker,             # args[6]
+            all_tools,                    # args[7]
+            server_conversation_tracker,  # args[8] (optional)
+        )
+        """
+        streamed_result = args[0] if len(args) > 0 else kwargs.get("streamed_result")
+        agent = args[1] if len(args) > 1 else kwargs.get("agent")
+        context_wrapper = args[3] if len(args) > 3 else kwargs.get("context_wrapper")
+        should_run_agent_start_hooks = bool(
+            args[5]
+            if len(args) > 5
+            else kwargs.get("should_run_agent_start_hooks", False)
+        )
+
+        span_kwargs: "dict[str, Any]" = {}
+        if streamed_result and hasattr(streamed_result, "input"):
+            span_kwargs["original_input"] = streamed_result.input
+
+        span = _maybe_start_agent_span(
+            context_wrapper,
+            agent,
+            should_run_agent_start_hooks,
+            span_kwargs,
+            is_streaming=True,
+        )
+
+        try:
+            result = await original_run_single_turn_streamed(*args, **kwargs)
+        except Exception as exc:
+            exc_info = sys.exc_info()
+            with capture_internal_exceptions():
+                if span is not None and span.timestamp is None:
+                    _record_exception_on_span(span, exc)
+                    end_invoke_agent_span(context_wrapper, agent)
+                _close_streaming_workflow_span(agent)
+            reraise(*exc_info)
 
         return result
 
     # Apply patches
     agents.run.AgentRunner._run_single_turn = classmethod(patched_run_single_turn)
+    agents.run.AgentRunner._run_single_turn_streamed = classmethod(
+        patched_run_single_turn_streamed
+    )
     agents._run_impl.RunImpl.execute_handoffs = classmethod(patched_execute_handoffs)
     agents._run_impl.RunImpl.execute_final_output = classmethod(
         patched_execute_final_output
diff --git a/sentry_sdk/integrations/openai_agents/patches/models.py b/sentry_sdk/integrations/openai_agents/patches/models.py
index a9b3c16a22..9b57a55f1f 100644
--- a/sentry_sdk/integrations/openai_agents/patches/models.py
+++ b/sentry_sdk/integrations/openai_agents/patches/models.py
@@ -1,23 +1,71 @@
 import copy
+import time
 from functools import wraps
 
 from sentry_sdk.integrations import DidNotEnable
 
 from ..spans import ai_client_span, update_ai_client_span
+
+import sentry_sdk
 from sentry_sdk.consts import SPANDATA
+from sentry_sdk.utils import logger
+from sentry_sdk.tracing import BAGGAGE_HEADER_NAME
+from sentry_sdk.tracing_utils import (
+    should_propagate_trace,
+    add_sentry_baggage_to_headers,
+)
 
 from typing import TYPE_CHECKING
 
 if TYPE_CHECKING:
-    from typing import Any, Callable
-
+    from typing import Any, Callable, Optional
+    from sentry_sdk.tracing import Span
 
 try:
     import agents
+    from agents.tool import HostedMCPTool
 except ImportError:
     raise DidNotEnable("OpenAI Agents not installed")
 
 
+def _set_response_model_on_agent_span(
+    agent: "agents.Agent", response_model: "Optional[str]"
+) -> None:
+    """Set the response model on the agent's invoke_agent span if available."""
+    if response_model:
+        agent_span = getattr(agent, "_sentry_agent_span", None)
+        if agent_span:
+            agent_span.set_data(SPANDATA.GEN_AI_RESPONSE_MODEL, response_model)
+
+
+def _inject_trace_propagation_headers(
+    hosted_tool: "HostedMCPTool", span: "Span"
+) -> None:
+    headers = hosted_tool.tool_config.get("headers")
+    if headers is None:
+        headers = {}
+        hosted_tool.tool_config["headers"] = headers
+
+    mcp_url = hosted_tool.tool_config.get("server_url")
+    if not mcp_url:
+        return
+
+    if should_propagate_trace(sentry_sdk.get_client(), mcp_url):
+        for (
+            key,
+            value,
+        ) in sentry_sdk.get_current_scope().iter_trace_propagation_headers(span=span):
+            logger.debug(
+                "[Tracing] Adding `{key}` header {value} to outgoing request to {mcp_url}.".format(
+                    key=key, value=value, mcp_url=mcp_url
+                )
+            )
+            if key == BAGGAGE_HEADER_NAME:
+                add_sentry_baggage_to_headers(headers, value)
+            else:
+                headers[key] = value
+
+
 def _create_get_model_wrapper(
     original_get_model: "Callable[..., Any]",
 ) -> "Callable[..., Any]":
@@ -37,15 +85,19 @@ def wrapped_get_model(
         # because we only patch its direct methods, all underlying data can remain unchanged.
         model = copy.copy(original_get_model(agent, run_config))
 
-        # Wrap _fetch_response if it exists (for OpenAI models) to capture raw response model
+        # Capture the request model name for spans (agent.model can be None when using defaults)
+        request_model_name = model.model if hasattr(model, "model") else str(model)
+        agent._sentry_request_model = request_model_name
+
+        # Wrap _fetch_response if it exists (for OpenAI models) to capture response model
         if hasattr(model, "_fetch_response"):
             original_fetch_response = model._fetch_response
 
             @wraps(original_fetch_response)
             async def wrapped_fetch_response(*args: "Any", **kwargs: "Any") -> "Any":
                 response = await original_fetch_response(*args, **kwargs)
-                if hasattr(response, "model"):
-                    agent._sentry_raw_response_model = str(response.model)
+                if hasattr(response, "model") and response.model:
+                    agent._sentry_response_model = str(response.model)
                 return response
 
             model._fetch_response = wrapped_fetch_response
@@ -54,25 +106,80 @@ async def wrapped_fetch_response(*args: "Any", **kwargs: "Any") -> "Any":
 
         @wraps(original_get_response)
         async def wrapped_get_response(*args: "Any", **kwargs: "Any") -> "Any":
+            mcp_tools = kwargs.get("tools")
+            hosted_tools = []
+            if mcp_tools is not None:
+                hosted_tools = [
+                    tool for tool in mcp_tools if isinstance(tool, HostedMCPTool)
+                ]
+
             with ai_client_span(agent, kwargs) as span:
+                for hosted_tool in hosted_tools:
+                    _inject_trace_propagation_headers(hosted_tool, span=span)
+
                 result = await original_get_response(*args, **kwargs)
 
-                response_model = getattr(agent, "_sentry_raw_response_model", None)
+                # Get response model captured from _fetch_response and clean up
+                response_model = getattr(agent, "_sentry_response_model", None)
                 if response_model:
-                    agent_span = getattr(agent, "_sentry_agent_span", None)
-                    if agent_span:
-                        agent_span.set_data(
-                            SPANDATA.GEN_AI_RESPONSE_MODEL, response_model
-                        )
-
-                    delattr(agent, "_sentry_raw_response_model")
+                    delattr(agent, "_sentry_response_model")
 
-                update_ai_client_span(span, agent, kwargs, result, response_model)
+                _set_response_model_on_agent_span(agent, response_model)
+                update_ai_client_span(span, result, response_model)
 
             return result
 
         model.get_response = wrapped_get_response
 
+        # Also wrap stream_response for streaming support
+        if hasattr(model, "stream_response"):
+            original_stream_response = model.stream_response
+
+            @wraps(original_stream_response)
+            async def wrapped_stream_response(*args: "Any", **kwargs: "Any") -> "Any":
+                # Uses explicit try/finally instead of context manager to ensure cleanup
+                # even if the consumer abandons the stream (GeneratorExit).
+                span_kwargs = dict(kwargs)
+                if len(args) > 0:
+                    span_kwargs["system_instructions"] = args[0]
+                if len(args) > 1:
+                    span_kwargs["input"] = args[1]
+
+                with ai_client_span(agent, span_kwargs) as span:
+                    span.set_data(SPANDATA.GEN_AI_RESPONSE_STREAMING, True)
+
+                    streaming_response = None
+                    ttft_recorded = False
+                    # Capture start time locally to avoid race conditions with concurrent requests
+                    start_time = time.perf_counter()
+
+                    async for event in original_stream_response(*args, **kwargs):
+                        # Detect first content token (text delta event)
+                        if not ttft_recorded and hasattr(event, "delta"):
+                            ttft = time.perf_counter() - start_time
+                            span.set_data(
+                                SPANDATA.GEN_AI_RESPONSE_TIME_TO_FIRST_TOKEN, ttft
+                            )
+                            ttft_recorded = True
+
+                        # Capture the full response from ResponseCompletedEvent
+                        if hasattr(event, "response"):
+                            streaming_response = event.response
+                        yield event
+
+                    # Update span with response data (usage, output, model)
+                    if streaming_response:
+                        response_model = (
+                            str(streaming_response.model)
+                            if hasattr(streaming_response, "model")
+                            and streaming_response.model
+                            else None
+                        )
+                        _set_response_model_on_agent_span(agent, response_model)
+                        update_ai_client_span(span, streaming_response)
+
+            model.stream_response = wrapped_stream_response
+
         return model
 
     return wrapped_get_model
diff --git a/sentry_sdk/integrations/openai_agents/patches/runner.py b/sentry_sdk/integrations/openai_agents/patches/runner.py
index 1d3bbc894b..fd3bc284e9 100644
--- a/sentry_sdk/integrations/openai_agents/patches/runner.py
+++ b/sentry_sdk/integrations/openai_agents/patches/runner.py
@@ -1,7 +1,9 @@
+import sys
 from functools import wraps
 
 import sentry_sdk
 from sentry_sdk.integrations import DidNotEnable
+from sentry_sdk.utils import capture_internal_exceptions, reraise
 
 from ..spans import agent_workflow_span, end_invoke_agent_span
 from ..utils import _capture_exception, _record_exception_on_span
@@ -14,7 +16,7 @@
 from typing import TYPE_CHECKING
 
 if TYPE_CHECKING:
-    from typing import Any, Callable
+    from typing import Any, AsyncIterator, Callable
 
 
 def _create_run_wrapper(original_func: "Callable[..., Any]") -> "Callable[..., Any]":
@@ -37,30 +39,110 @@ async def wrapper(*args: "Any", **kwargs: "Any") -> "Any":
                 try:
                     run_result = await original_func(*args, **kwargs)
                 except AgentsException as exc:
-                    _capture_exception(exc)
-
-                    context_wrapper = getattr(exc.run_data, "context_wrapper", None)
-                    if context_wrapper is not None:
-                        invoke_agent_span = getattr(
-                            context_wrapper, "_sentry_agent_span", None
-                        )
-
-                        if (
-                            invoke_agent_span is not None
-                            and invoke_agent_span.timestamp is None
-                        ):
-                            _record_exception_on_span(invoke_agent_span, exc)
-                            end_invoke_agent_span(context_wrapper, agent)
-
-                    raise exc from None
+                    exc_info = sys.exc_info()
+                    with capture_internal_exceptions():
+                        _capture_exception(exc)
+
+                        context_wrapper = getattr(exc.run_data, "context_wrapper", None)
+                        if context_wrapper is not None:
+                            invoke_agent_span = getattr(
+                                context_wrapper, "_sentry_agent_span", None
+                            )
+
+                            if (
+                                invoke_agent_span is not None
+                                and invoke_agent_span.timestamp is None
+                            ):
+                                _record_exception_on_span(invoke_agent_span, exc)
+                                end_invoke_agent_span(context_wrapper, agent)
+                    reraise(*exc_info)
                 except Exception as exc:
-                    # Invoke agent span is not finished in this case.
-                    # This is much less likely to occur than other cases because
-                    # AgentRunner.run() is "just" a while loop around _run_single_turn.
-                    _capture_exception(exc)
-                    raise exc from None
+                    exc_info = sys.exc_info()
+                    with capture_internal_exceptions():
+                        # Invoke agent span is not finished in this case.
+                        # This is much less likely to occur than other cases because
+                        # AgentRunner.run() is "just" a while loop around _run_single_turn.
+                        _capture_exception(exc)
+                    reraise(*exc_info)
 
                 end_invoke_agent_span(run_result.context_wrapper, agent)
                 return run_result
 
     return wrapper
+
+
+def _create_run_streamed_wrapper(
+    original_func: "Callable[..., Any]",
+) -> "Callable[..., Any]":
+    """
+    Wraps the agents.Runner.run_streamed method to create a root span for streaming agent workflow runs.
+
+    Unlike run(), run_streamed() returns immediately with a RunResultStreaming object
+    while execution continues in a background task. The workflow span must stay open
+    throughout the streaming operation and close when streaming completes or is abandoned.
+
+    Note: We don't use isolation_scope() here because it uses context variables that
+    cannot span async boundaries (the __enter__ and __exit__ would be called from
+    different async contexts, causing ValueError).
+    """
+
+    @wraps(original_func)
+    def wrapper(*args: "Any", **kwargs: "Any") -> "Any":
+        # Clone agent because agent invocation spans are attached per run.
+        agent = args[0].clone()
+
+        # Start workflow span immediately (before run_streamed returns)
+        workflow_span = agent_workflow_span(agent)
+        workflow_span.__enter__()
+
+        # Store span on agent for cleanup
+        agent._sentry_workflow_span = workflow_span
+
+        args = (agent, *args[1:])
+
+        try:
+            # Call original function to get RunResultStreaming
+            run_result = original_func(*args, **kwargs)
+        except Exception as exc:
+            # If run_streamed itself fails (not the background task), clean up immediately
+            workflow_span.__exit__(*sys.exc_info())
+            _capture_exception(exc)
+            raise
+
+        def _close_workflow_span() -> None:
+            if hasattr(agent, "_sentry_workflow_span"):
+                workflow_span.__exit__(*sys.exc_info())
+                delattr(agent, "_sentry_workflow_span")
+
+        if hasattr(run_result, "stream_events"):
+            original_stream_events = run_result.stream_events
+
+            @wraps(original_stream_events)
+            async def wrapped_stream_events(
+                *stream_args: "Any", **stream_kwargs: "Any"
+            ) -> "AsyncIterator[Any]":
+                try:
+                    async for event in original_stream_events(
+                        *stream_args, **stream_kwargs
+                    ):
+                        yield event
+                finally:
+                    _close_workflow_span()
+
+            run_result.stream_events = wrapped_stream_events
+
+        if hasattr(run_result, "cancel"):
+            original_cancel = run_result.cancel
+
+            @wraps(original_cancel)
+            def wrapped_cancel(*cancel_args: "Any", **cancel_kwargs: "Any") -> "Any":
+                try:
+                    return original_cancel(*cancel_args, **cancel_kwargs)
+                finally:
+                    _close_workflow_span()
+
+            run_result.cancel = wrapped_cancel
+
+        return run_result
+
+    return wrapper
diff --git a/sentry_sdk/integrations/openai_agents/spans/ai_client.py b/sentry_sdk/integrations/openai_agents/spans/ai_client.py
index 1e188aa097..c099f133f4 100644
--- a/sentry_sdk/integrations/openai_agents/spans/ai_client.py
+++ b/sentry_sdk/integrations/openai_agents/spans/ai_client.py
@@ -21,7 +21,13 @@ def ai_client_span(
     agent: "Agent", get_response_kwargs: "dict[str, Any]"
 ) -> "sentry_sdk.tracing.Span":
     # TODO-anton: implement other types of operations. Now "chat" is hardcoded.
-    model_name = agent.model.model if hasattr(agent.model, "model") else agent.model
+    # Get model name from agent.model or fall back to request model (for when agent.model is None/default)
+    model_name = None
+    if agent.model:
+        model_name = agent.model.model if hasattr(agent.model, "model") else agent.model
+    elif hasattr(agent, "_sentry_request_model"):
+        model_name = agent._sentry_request_model
+
     span = sentry_sdk.start_span(
         op=OP.GEN_AI_CHAT,
         description=f"chat {model_name}",
@@ -38,15 +44,18 @@ def ai_client_span(
 
 def update_ai_client_span(
     span: "sentry_sdk.tracing.Span",
-    agent: "Agent",
-    get_response_kwargs: "dict[str, Any]",
-    result: "Any",
+    response: "Any",
     response_model: "Optional[str]" = None,
 ) -> None:
-    _set_usage_data(span, result.usage)
-    _set_output_data(span, result)
-    _create_mcp_execute_tool_spans(span, result)
+    """Update AI client span with response data (works for streaming and non-streaming)."""
+    if hasattr(response, "usage") and response.usage:
+        _set_usage_data(span, response.usage)
+
+    if hasattr(response, "output") and response.output:
+        _set_output_data(span, response)
+        _create_mcp_execute_tool_spans(span, response)
 
-    # Set response model if captured from raw response
     if response_model is not None:
         span.set_data(SPANDATA.GEN_AI_RESPONSE_MODEL, response_model)
+    elif hasattr(response, "model") and response.model:
+        span.set_data(SPANDATA.GEN_AI_RESPONSE_MODEL, str(response.model))
diff --git a/sentry_sdk/integrations/openai_agents/utils.py b/sentry_sdk/integrations/openai_agents/utils.py
index a24d0e909d..f3873db886 100644
--- a/sentry_sdk/integrations/openai_agents/utils.py
+++ b/sentry_sdk/integrations/openai_agents/utils.py
@@ -1,3 +1,5 @@
+import json
+
 import sentry_sdk
 from sentry_sdk.ai.utils import (
     GEN_AI_ALLOWED_MESSAGE_ROLES,
@@ -11,14 +13,20 @@
 from sentry_sdk.scope import should_send_default_pii
 from sentry_sdk.tracing_utils import set_span_errored
 from sentry_sdk.utils import event_from_exception, safe_serialize
+from sentry_sdk.ai._openai_completions_api import _transform_system_instructions
+from sentry_sdk.ai._openai_responses_api import (
+    _is_system_instruction,
+    _get_system_instructions,
+)
 
 from typing import TYPE_CHECKING
 
 if TYPE_CHECKING:
     from typing import Any
-    from agents import Usage
+    from agents import Usage, TResponseInputItem
 
     from sentry_sdk.tracing import Span
+    from sentry_sdk._types import TextPart
 
 try:
     import agents
@@ -63,8 +71,14 @@ def _set_agent_data(span: "sentry_sdk.tracing.Span", agent: "agents.Agent") -> N
             SPANDATA.GEN_AI_REQUEST_MAX_TOKENS, agent.model_settings.max_tokens
         )
 
+    # Get model name from agent.model or fall back to request model (for when agent.model is None/default)
+    model_name = None
     if agent.model:
         model_name = agent.model.model if hasattr(agent.model, "model") else agent.model
+    elif hasattr(agent, "_sentry_request_model"):
+        model_name = agent._sentry_request_model
+
+    if model_name:
         span.set_data(SPANDATA.GEN_AI_REQUEST_MODEL, model_name)
 
     if agent.model_settings.presence_penalty:
@@ -115,19 +129,37 @@ def _set_input_data(
         return
     request_messages = []
 
-    system_instructions = get_response_kwargs.get("system_instructions")
-    if system_instructions:
-        request_messages.append(
+    messages: "str | list[TResponseInputItem]" = get_response_kwargs.get("input", [])
+
+    instructions_text_parts: "list[TextPart]" = []
+    explicit_instructions = get_response_kwargs.get("system_instructions")
+    if explicit_instructions is not None:
+        instructions_text_parts.append(
             {
-                "role": GEN_AI_ALLOWED_MESSAGE_ROLES.SYSTEM,
-                "content": [{"type": "text", "text": system_instructions}],
+                "type": "text",
+                "content": explicit_instructions,
             }
         )
 
-    for message in get_response_kwargs.get("input", []):
+    system_instructions = _get_system_instructions(messages)
+
+    # Deliberate use of function accepting completions API type because
+    # of shared structure FOR THIS PURPOSE ONLY.
+    instructions_text_parts += _transform_system_instructions(system_instructions)
+
+    if len(instructions_text_parts) > 0:
+        span.set_data(
+            SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS,
+            json.dumps(instructions_text_parts),
+        )
+
+    non_system_messages = [
+        message for message in messages if not _is_system_instruction(message)
+    ]
+    for message in non_system_messages:
         if "role" in message:
-            normalized_role = normalize_message_role(message.get("role"))
-            content = message.get("content")
+            normalized_role = normalize_message_role(message.get("role"))  # type: ignore
+            content = message.get("content")  # type: ignore
             request_messages.append(
                 {
                     "role": normalized_role,
@@ -139,14 +171,14 @@ def _set_input_data(
                 }
             )
         else:
-            if message.get("type") == "function_call":
+            if message.get("type") == "function_call":  # type: ignore
                 request_messages.append(
                     {
                         "role": GEN_AI_ALLOWED_MESSAGE_ROLES.ASSISTANT,
                         "content": [message],
                     }
                 )
-            elif message.get("type") == "function_call_output":
+            elif message.get("type") == "function_call_output":  # type: ignore
                 request_messages.append(
                     {
                         "role": GEN_AI_ALLOWED_MESSAGE_ROLES.TOOL,
diff --git a/sentry_sdk/integrations/pure_eval.py b/sentry_sdk/integrations/pure_eval.py
index 1f3a1f4ea1..f8c7a9fba6 100644
--- a/sentry_sdk/integrations/pure_eval.py
+++ b/sentry_sdk/integrations/pure_eval.py
@@ -15,12 +15,12 @@
     from sentry_sdk._types import Event, Hint
 
 try:
-    import executing
+    from executing import Source
 except ImportError:
     raise DidNotEnable("executing is not installed")
 
 try:
-    import pure_eval
+    from pure_eval import Evaluator
 except ImportError:
     raise DidNotEnable("pure_eval is not installed")
 
@@ -81,7 +81,7 @@ def add_executing_info(
 
 
 def pure_eval_frame(frame: "FrameType") -> "Dict[str, Any]":
-    source = executing.Source.for_frame(frame)
+    source = Source.for_frame(frame)
     if not source.tree:
         return {}
 
@@ -98,7 +98,7 @@ def pure_eval_frame(frame: "FrameType") -> "Dict[str, Any]":
         if isinstance(scope, (ast.FunctionDef, ast.ClassDef, ast.Module)):
             break
 
-    evaluator = pure_eval.Evaluator.from_frame(frame)
+    evaluator = Evaluator.from_frame(frame)
     expressions = evaluator.interesting_expressions_grouped(scope)
 
     def closeness(expression: "Tuple[List[Any], Any]") -> "Tuple[int, int]":
diff --git a/sentry_sdk/integrations/pydantic_ai/patches/agent_run.py b/sentry_sdk/integrations/pydantic_ai/patches/agent_run.py
index d158d892d5..eaa4385834 100644
--- a/sentry_sdk/integrations/pydantic_ai/patches/agent_run.py
+++ b/sentry_sdk/integrations/pydantic_ai/patches/agent_run.py
@@ -1,7 +1,9 @@
+import sys
 from functools import wraps
 
 import sentry_sdk
 from sentry_sdk.integrations import DidNotEnable
+from sentry_sdk.utils import capture_internal_exceptions, reraise
 
 from ..spans import invoke_agent_span, update_invoke_agent_span
 from ..utils import _capture_exception, pop_agent, push_agent
@@ -121,8 +123,10 @@ async def wrapper(self: "Any", *args: "Any", **kwargs: "Any") -> "Any":
 
                     return result
                 except Exception as exc:
-                    _capture_exception(exc)
-                    raise exc from None
+                    exc_info = sys.exc_info()
+                    with capture_internal_exceptions():
+                        _capture_exception(exc)
+                    reraise(*exc_info)
                 finally:
                     # Pop agent from contextvar stack
                     pop_agent()
@@ -177,8 +181,10 @@ async def wrapper(self: "Any", *args: "Any", **kwargs: "Any") -> "Any":
             async for event in original_func(self, *args, **kwargs):
                 yield event
         except Exception as exc:
-            _capture_exception(exc)
-            raise exc from None
+            exc_info = sys.exc_info()
+            with capture_internal_exceptions():
+                _capture_exception(exc)
+            reraise(*exc_info)
 
     return wrapper
 
diff --git a/sentry_sdk/integrations/pydantic_ai/patches/tools.py b/sentry_sdk/integrations/pydantic_ai/patches/tools.py
index b826a543fc..394d44f0f3 100644
--- a/sentry_sdk/integrations/pydantic_ai/patches/tools.py
+++ b/sentry_sdk/integrations/pydantic_ai/patches/tools.py
@@ -1,7 +1,9 @@
+import sys
 from functools import wraps
 
 from sentry_sdk.integrations import DidNotEnable
 import sentry_sdk
+from sentry_sdk.utils import capture_internal_exceptions, reraise
 
 from ..spans import execute_tool_span, update_execute_tool_span
 from ..utils import _capture_exception, get_current_agent
@@ -81,21 +83,22 @@ async def wrapped_call_tool(
                         update_execute_tool_span(span, result)
                         return result
                     except ToolRetryError as exc:
-                        # Avoid circular import due to multi-file integration structure
-                        from sentry_sdk.integrations.pydantic_ai import (
-                            PydanticAIIntegration,
-                        )
-
-                        integration = sentry_sdk.get_client().get_integration(
-                            PydanticAIIntegration
-                        )
-                        if (
-                            integration is None
-                            or not integration.handled_tool_call_exceptions
-                        ):
-                            raise exc from None
-                        _capture_exception(exc, handled=True)
-                        raise exc from None
+                        exc_info = sys.exc_info()
+                        with capture_internal_exceptions():
+                            # Avoid circular import due to multi-file integration structure
+                            from sentry_sdk.integrations.pydantic_ai import (
+                                PydanticAIIntegration,
+                            )
+
+                            integration = sentry_sdk.get_client().get_integration(
+                                PydanticAIIntegration
+                            )
+                            if (
+                                integration is not None
+                                and integration.handled_tool_call_exceptions
+                            ):
+                                _capture_exception(exc, handled=True)
+                        reraise(*exc_info)
 
         # No span context - just call original
         return await original_call_tool(
diff --git a/sentry_sdk/integrations/pydantic_ai/spans/ai_client.py b/sentry_sdk/integrations/pydantic_ai/spans/ai_client.py
index cb34f36e4f..b2ae15b38f 100644
--- a/sentry_sdk/integrations/pydantic_ai/spans/ai_client.py
+++ b/sentry_sdk/integrations/pydantic_ai/spans/ai_client.py
@@ -1,5 +1,13 @@
+import json
+
 import sentry_sdk
-from sentry_sdk.ai.utils import set_data_normalized
+from sentry_sdk._types import BLOB_DATA_SUBSTITUTE
+from sentry_sdk.ai.utils import (
+    normalize_message_roles,
+    set_data_normalized,
+    truncate_and_annotate_messages,
+    get_modality_from_mime_type,
+)
 from sentry_sdk.consts import OP, SPANDATA
 from sentry_sdk.utils import safe_serialize
 
@@ -20,15 +28,18 @@
 if TYPE_CHECKING:
     from typing import Any, List, Dict
     from pydantic_ai.usage import RequestUsage  # type: ignore
+    from pydantic_ai.messages import ModelMessage, SystemPromptPart  # type: ignore
+    from sentry_sdk._types import TextPart as SentryTextPart
 
 try:
-    from pydantic_ai.messages import (  # type: ignore
+    from pydantic_ai.messages import (
         BaseToolCallPart,
         BaseToolReturnPart,
         SystemPromptPart,
         UserPromptPart,
         TextPart,
         ThinkingPart,
+        BinaryContent,
     )
 except ImportError:
     # Fallback if these classes are not available
@@ -38,6 +49,48 @@
     UserPromptPart = None
     TextPart = None
     ThinkingPart = None
+    BinaryContent = None
+
+
+def _transform_system_instructions(
+    permanent_instructions: "list[SystemPromptPart]",
+    current_instructions: "list[str]",
+) -> "list[SentryTextPart]":
+    text_parts: "list[SentryTextPart]" = [
+        {
+            "type": "text",
+            "content": instruction.content,
+        }
+        for instruction in permanent_instructions
+    ]
+
+    text_parts.extend(
+        {
+            "type": "text",
+            "content": instruction,
+        }
+        for instruction in current_instructions
+    )
+
+    return text_parts
+
+
+def _get_system_instructions(
+    messages: "list[ModelMessage]",
+) -> "tuple[list[SystemPromptPart], list[str]]":
+    permanent_instructions = []
+    current_instructions = []
+
+    for msg in messages:
+        if hasattr(msg, "parts"):
+            for part in msg.parts:
+                if SystemPromptPart and isinstance(part, SystemPromptPart):
+                    permanent_instructions.append(part)
+
+        if hasattr(msg, "instructions") and msg.instructions is not None:
+            current_instructions.append(msg.instructions)
+
+    return permanent_instructions, current_instructions
 
 
 def _set_input_messages(span: "sentry_sdk.tracing.Span", messages: "Any") -> None:
@@ -48,21 +101,19 @@ def _set_input_messages(span: "sentry_sdk.tracing.Span", messages: "Any") -> Non
     if not messages:
         return
 
+    permanent_instructions, current_instructions = _get_system_instructions(messages)
+    if len(permanent_instructions) > 0 or len(current_instructions) > 0:
+        span.set_data(
+            SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS,
+            json.dumps(
+                _transform_system_instructions(
+                    permanent_instructions, current_instructions
+                )
+            ),
+        )
+
     try:
         formatted_messages = []
-        system_prompt = None
-
-        # Extract system prompt from any ModelRequest with instructions
-        for msg in messages:
-            if hasattr(msg, "instructions") and msg.instructions:
-                system_prompt = msg.instructions
-                break
-
-        # Add system prompt as first message if present
-        if system_prompt:
-            formatted_messages.append(
-                {"role": "system", "content": [{"type": "text", "text": system_prompt}]}
-            )
 
         for msg in messages:
             if hasattr(msg, "parts"):
@@ -70,7 +121,7 @@ def _set_input_messages(span: "sentry_sdk.tracing.Span", messages: "Any") -> Non
                     role = "user"
                     # Use isinstance checks with proper base classes
                     if SystemPromptPart and isinstance(part, SystemPromptPart):
-                        role = "system"
+                        continue
                     elif (
                         (TextPart and isinstance(part, TextPart))
                         or (ThinkingPart and isinstance(part, ThinkingPart))
@@ -107,6 +158,17 @@ def _set_input_messages(span: "sentry_sdk.tracing.Span", messages: "Any") -> Non
                             for item in part.content:
                                 if isinstance(item, str):
                                     content.append({"type": "text", "text": item})
+                                elif BinaryContent and isinstance(item, BinaryContent):
+                                    content.append(
+                                        {
+                                            "type": "blob",
+                                            "modality": get_modality_from_mime_type(
+                                                item.media_type
+                                            ),
+                                            "mime_type": item.media_type,
+                                            "content": BLOB_DATA_SUBSTITUTE,
+                                        }
+                                    )
                                 else:
                                     content.append(safe_serialize(item))
                         else:
@@ -124,8 +186,13 @@ def _set_input_messages(span: "sentry_sdk.tracing.Span", messages: "Any") -> Non
                         formatted_messages.append(message)
 
         if formatted_messages:
+            normalized_messages = normalize_message_roles(formatted_messages)
+            scope = sentry_sdk.get_current_scope()
+            messages_data = truncate_and_annotate_messages(
+                normalized_messages, span, scope
+            )
             set_data_normalized(
-                span, SPANDATA.GEN_AI_REQUEST_MESSAGES, formatted_messages, unpack=False
+                span, SPANDATA.GEN_AI_REQUEST_MESSAGES, messages_data, unpack=False
             )
     except Exception:
         # If we fail to format messages, just skip it
diff --git a/sentry_sdk/integrations/pydantic_ai/spans/invoke_agent.py b/sentry_sdk/integrations/pydantic_ai/spans/invoke_agent.py
index 629b3d1206..b4f8307170 100644
--- a/sentry_sdk/integrations/pydantic_ai/spans/invoke_agent.py
+++ b/sentry_sdk/integrations/pydantic_ai/spans/invoke_agent.py
@@ -1,5 +1,12 @@
 import sentry_sdk
-from sentry_sdk.ai.utils import get_start_span_function, set_data_normalized
+from sentry_sdk._types import BLOB_DATA_SUBSTITUTE
+from sentry_sdk.ai.utils import (
+    get_modality_from_mime_type,
+    get_start_span_function,
+    normalize_message_roles,
+    set_data_normalized,
+    truncate_and_annotate_messages,
+)
 from sentry_sdk.consts import OP, SPANDATA
 
 from ..consts import SPAN_ORIGIN
@@ -16,6 +23,11 @@
 if TYPE_CHECKING:
     from typing import Any
 
+try:
+    from pydantic_ai.messages import BinaryContent  # type: ignore
+except ImportError:
+    BinaryContent = None
+
 
 def invoke_agent_span(
     user_prompt: "Any",
@@ -93,6 +105,17 @@ def invoke_agent_span(
                 for item in user_prompt:
                     if isinstance(item, str):
                         content.append({"text": item, "type": "text"})
+                    elif BinaryContent and isinstance(item, BinaryContent):
+                        content.append(
+                            {
+                                "type": "blob",
+                                "modality": get_modality_from_mime_type(
+                                    item.media_type
+                                ),
+                                "mime_type": item.media_type,
+                                "content": BLOB_DATA_SUBSTITUTE,
+                            }
+                        )
                 if content:
                     messages.append(
                         {
@@ -102,8 +125,13 @@ def invoke_agent_span(
                     )
 
         if messages:
+            normalized_messages = normalize_message_roles(messages)
+            scope = sentry_sdk.get_current_scope()
+            messages_data = truncate_and_annotate_messages(
+                normalized_messages, span, scope
+            )
             set_data_normalized(
-                span, SPANDATA.GEN_AI_REQUEST_MESSAGES, messages, unpack=False
+                span, SPANDATA.GEN_AI_REQUEST_MESSAGES, messages_data, unpack=False
             )
 
     return span
diff --git a/sentry_sdk/integrations/pydantic_ai/spans/utils.py b/sentry_sdk/integrations/pydantic_ai/spans/utils.py
index c70afd5f31..4a8ad4c68c 100644
--- a/sentry_sdk/integrations/pydantic_ai/spans/utils.py
+++ b/sentry_sdk/integrations/pydantic_ai/spans/utils.py
@@ -6,7 +6,7 @@
 from typing import TYPE_CHECKING
 
 if TYPE_CHECKING:
-    from typing import Union
+    from typing import Union, Dict, Any, List
     from pydantic_ai.usage import RequestUsage, RunUsage  # type: ignore
 
 
@@ -28,6 +28,19 @@ def _set_usage_data(
     if hasattr(usage, "input_tokens") and usage.input_tokens is not None:
         span.set_data(SPANDATA.GEN_AI_USAGE_INPUT_TOKENS, usage.input_tokens)
 
+    # Pydantic AI uses cache_read_tokens (not input_tokens_cached)
+    if hasattr(usage, "cache_read_tokens") and usage.cache_read_tokens is not None:
+        span.set_data(
+            SPANDATA.GEN_AI_USAGE_INPUT_TOKENS_CACHED, usage.cache_read_tokens
+        )
+
+    # Pydantic AI uses cache_write_tokens (not input_tokens_cache_write)
+    if hasattr(usage, "cache_write_tokens") and usage.cache_write_tokens is not None:
+        span.set_data(
+            SPANDATA.GEN_AI_USAGE_INPUT_TOKENS_CACHE_WRITE,
+            usage.cache_write_tokens,
+        )
+
     if hasattr(usage, "output_tokens") and usage.output_tokens is not None:
         span.set_data(SPANDATA.GEN_AI_USAGE_OUTPUT_TOKENS, usage.output_tokens)
 
diff --git a/sentry_sdk/integrations/ray.py b/sentry_sdk/integrations/ray.py
index 92a35546ab..d1559d5c19 100644
--- a/sentry_sdk/integrations/ray.py
+++ b/sentry_sdk/integrations/ray.py
@@ -16,6 +16,7 @@
 
 try:
     import ray  # type: ignore[import-not-found]
+    from ray import remote
 except ImportError:
     raise DidNotEnable("Ray not installed.")
 
@@ -36,8 +37,28 @@ def _check_sentry_initialized() -> None:
     )
 
 
+def _insert_sentry_tracing_in_signature(func: "Callable[..., Any]") -> None:
+    # Patching new_func signature to add the _sentry_tracing parameter to it
+    # Ray later inspects the signature and finds the unexpected parameter otherwise
+    signature = inspect.signature(func)
+    params = list(signature.parameters.values())
+    sentry_tracing_param = inspect.Parameter(
+        "_sentry_tracing",
+        kind=inspect.Parameter.KEYWORD_ONLY,
+        default=None,
+    )
+
+    # Keyword only arguments are penultimate if function has variadic keyword arguments
+    if params and params[-1].kind is inspect.Parameter.VAR_KEYWORD:
+        params.insert(-1, sentry_tracing_param)
+    else:
+        params.append(sentry_tracing_param)
+
+    func.__signature__ = signature.replace(parameters=params)  # type: ignore[attr-defined]
+
+
 def _patch_ray_remote() -> None:
-    old_remote = ray.remote
+    old_remote = remote
 
     @functools.wraps(old_remote)
     def new_remote(
@@ -86,18 +107,7 @@ def new_func(
 
                     return result
 
-            # Patching new_func signature to add the _sentry_tracing parameter to it
-            # Ray later inspects the signature and finds the unexpected parameter otherwise
-            signature = inspect.signature(new_func)
-            params = list(signature.parameters.values())
-            params.append(
-                inspect.Parameter(
-                    "_sentry_tracing",
-                    kind=inspect.Parameter.KEYWORD_ONLY,
-                    default=None,
-                )
-            )
-            new_func.__signature__ = signature.replace(parameters=params)  # type: ignore[attr-defined]
+            _insert_sentry_tracing_in_signature(new_func)
 
             if f:
                 rv = old_remote(new_func)
diff --git a/sentry_sdk/integrations/stdlib.py b/sentry_sdk/integrations/stdlib.py
index bf0c626fa8..e3120a3b32 100644
--- a/sentry_sdk/integrations/stdlib.py
+++ b/sentry_sdk/integrations/stdlib.py
@@ -69,10 +69,17 @@ def _install_httplib() -> None:
     def putrequest(
         self: "HTTPConnection", method: str, url: str, *args: "Any", **kwargs: "Any"
     ) -> "Any":
-        host = self.host
-        port = self.port
         default_port = self.default_port
 
+        # proxies go through set_tunnel
+        tunnel_host = getattr(self, "_tunnel_host", None)
+        if tunnel_host:
+            host = tunnel_host
+            port = getattr(self, "_tunnel_port", default_port)
+        else:
+            host = self.host
+            port = self.port
+
         client = sentry_sdk.get_client()
         if client.get_integration(StdlibIntegration) is None or is_sentry_url(
             client, host
@@ -104,6 +111,11 @@ def putrequest(
             span.set_data(SPANDATA.HTTP_QUERY, parsed_url.query)
             span.set_data(SPANDATA.HTTP_FRAGMENT, parsed_url.fragment)
 
+        # for proxies, these point to the proxy host/port
+        if tunnel_host:
+            span.set_data(SPANDATA.NETWORK_PEER_ADDRESS, self.host)
+            span.set_data(SPANDATA.NETWORK_PEER_PORT, self.port)
+
         rv = real_putrequest(self, method, url, *args, **kwargs)
 
         if should_propagate_trace(client, real_url):
diff --git a/sentry_sdk/integrations/threading.py b/sentry_sdk/integrations/threading.py
index 6311b935a0..5b5633507f 100644
--- a/sentry_sdk/integrations/threading.py
+++ b/sentry_sdk/integrations/threading.py
@@ -54,11 +54,14 @@ def setup_once() -> None:
 
         try:
             from django import VERSION as django_version  # noqa: N811
+        except ImportError:
+            django_version = None
+
+        try:
             import channels  # type: ignore[import-untyped]
 
             channels_version = channels.__version__
-        except ImportError:
-            django_version = None
+        except (ImportError, AttributeError):
             channels_version = None
 
         is_async_emulated_with_threads = (
diff --git a/sentry_sdk/integrations/typer.py b/sentry_sdk/integrations/typer.py
index be3d7d1d68..2865f3ee6f 100644
--- a/sentry_sdk/integrations/typer.py
+++ b/sentry_sdk/integrations/typer.py
@@ -22,6 +22,7 @@
 
 try:
     import typer
+    from typer.main import except_hook
 except ImportError:
     raise DidNotEnable("Typer not installed")
 
@@ -31,7 +32,7 @@ class TyperIntegration(Integration):
 
     @staticmethod
     def setup_once() -> None:
-        typer.main.except_hook = _make_excepthook(typer.main.except_hook)  # type: ignore
+        typer.main.except_hook = _make_excepthook(except_hook)  # type: ignore
 
 
 def _make_excepthook(old_excepthook: "Excepthook") -> "Excepthook":
diff --git a/sentry_sdk/metrics.py b/sentry_sdk/metrics.py
index 30f8191126..167e49da05 100644
--- a/sentry_sdk/metrics.py
+++ b/sentry_sdk/metrics.py
@@ -1,8 +1,3 @@
-"""
-NOTE: This file contains experimental code that may be changed or removed at any
-time without prior notice.
-"""
-
 import time
 from typing import Any, Optional, TYPE_CHECKING, Union
 
diff --git a/sentry_sdk/scope.py b/sentry_sdk/scope.py
index 1c3fe884e8..3bc51c1af0 100644
--- a/sentry_sdk/scope.py
+++ b/sentry_sdk/scope.py
@@ -9,6 +9,7 @@
 from functools import wraps
 from itertools import chain
 
+import sentry_sdk
 from sentry_sdk._types import AnnotatedValue
 from sentry_sdk.attachments import Attachment
 from sentry_sdk.consts import (
@@ -28,9 +29,11 @@
 from sentry_sdk.tracing_utils import (
     Baggage,
     has_tracing_enabled,
+    has_span_streaming_enabled,
     normalize_incoming_data,
     PropagationContext,
 )
+from sentry_sdk.traces import StreamedSpan
 from sentry_sdk.tracing import (
     BAGGAGE_HEADER_NAME,
     SENTRY_TRACE_HEADER_NAME,
@@ -220,6 +223,7 @@ class Scope:
         "_breadcrumbs",
         "_n_breadcrumbs_truncated",
         "_gen_ai_original_message_count",
+        "_gen_ai_conversation_id",
         "_event_processors",
         "_error_processors",
         "_should_capture",
@@ -302,6 +306,8 @@ def __copy__(self) -> "Scope":
 
         rv._attributes = self._attributes.copy()
 
+        rv._gen_ai_conversation_id = self._gen_ai_conversation_id
+
         return rv
 
     @classmethod
@@ -365,6 +371,26 @@ def get_global_scope(cls) -> "Scope":
 
         return _global_scope
 
+    def set_global_attributes(self) -> None:
+        from sentry_sdk.client import SDK_INFO
+
+        self.set_attribute("sentry.sdk.name", SDK_INFO["name"])
+        self.set_attribute("sentry.sdk.version", SDK_INFO["version"])
+
+        options = sentry_sdk.get_client().options
+
+        server_name = options.get("server_name")
+        if server_name:
+            self.set_attribute(SPANDATA.SERVER_ADDRESS, server_name)
+
+        environment = options.get("environment")
+        if environment:
+            self.set_attribute("sentry.environment", environment)
+
+        release = options.get("release")
+        if release:
+            self.set_attribute("sentry.release", release)
+
     @classmethod
     def last_event_id(cls) -> "Optional[str]":
         """
@@ -467,7 +493,14 @@ def set_client(
             If `None` the client of the scope will be replaced by a :py:class:`sentry_sdk.NonRecordingClient`.
 
         """
-        self.client = client if client is not None else NonRecordingClient()
+        if client is not None:
+            self.client = client
+            # We need a client to set the initial global attributes on the global
+            # scope since they mostly come from client options, so populate them
+            # as soon as a client is set
+            sentry_sdk.get_global_scope().set_global_attributes()
+        else:
+            self.client = NonRecordingClient()
 
     def fork(self) -> "Scope":
         """
@@ -692,6 +725,8 @@ def clear(self) -> None:
 
         self._attributes: "Attributes" = {}
 
+        self._gen_ai_conversation_id: "Optional[str]" = None
+
     @_attr_setter
     def level(self, value: "LogLevelStr") -> None:
         """
@@ -884,6 +919,26 @@ def remove_extra(
         """Removes a specific extra key."""
         self._extras.pop(key, None)
 
+    def set_conversation_id(self, conversation_id: str) -> None:
+        """
+        Sets the conversation ID for gen_ai spans.
+
+        :param conversation_id: The conversation ID to set.
+        """
+        self._gen_ai_conversation_id = conversation_id
+
+    def get_conversation_id(self) -> "Optional[str]":
+        """
+        Gets the conversation ID for gen_ai spans.
+
+        :returns: The conversation ID, or None if not set.
+        """
+        return self._gen_ai_conversation_id
+
+    def remove_conversation_id(self) -> None:
+        """Removes the conversation ID."""
+        self._gen_ai_conversation_id = None
+
     def clear_breadcrumbs(self) -> None:
         """Clears breadcrumb buffer."""
         self._breadcrumbs: "Deque[Breadcrumb]" = deque()
@@ -1225,6 +1280,17 @@ def _capture_metric(self, metric: "Optional[Metric]") -> None:
 
         client._capture_metric(metric, scope=merged_scope)
 
+    def _capture_span(self, span: "Optional[StreamedSpan]") -> None:
+        if span is None:
+            return
+
+        client = self.get_client()
+        if not has_span_streaming_enabled(client.options):
+            return
+
+        merged_scope = self._merge_scopes()
+        client._capture_span(span, scope=merged_scope)
+
     def capture_message(
         self,
         message: str,
@@ -1468,44 +1534,26 @@ def _apply_flags_to_event(
                 {"values": flags}
             )
 
-    def _apply_global_attributes_to_telemetry(
-        self, telemetry: "Union[Log, Metric]"
-    ) -> None:
-        # TODO: Global stuff like this should just be retrieved at init time and
-        # put onto the global scope's attributes and then applied to events
-        # from there
-        from sentry_sdk.client import SDK_INFO
-
-        attributes = telemetry["attributes"]
-
-        attributes["sentry.sdk.name"] = SDK_INFO["name"]
-        attributes["sentry.sdk.version"] = SDK_INFO["version"]
-
-        options = self.get_client().options
-
-        server_name = options.get("server_name")
-        if server_name is not None and SPANDATA.SERVER_ADDRESS not in attributes:
-            attributes[SPANDATA.SERVER_ADDRESS] = server_name
-
-        environment = options.get("environment")
-        if environment is not None and "sentry.environment" not in attributes:
-            attributes["sentry.environment"] = environment
-
-        release = options.get("release")
-        if release is not None and "sentry.release" not in attributes:
-            attributes["sentry.release"] = release
-
     def _apply_scope_attributes_to_telemetry(
-        self, telemetry: "Union[Log, Metric]"
+        self, telemetry: "Union[Log, Metric, StreamedSpan]"
     ) -> None:
+        # TODO: turn Logs, Metrics into actual classes
+        if isinstance(telemetry, dict):
+            attributes = telemetry["attributes"]
+        else:
+            attributes = telemetry._attributes
+
         for attribute, value in self._attributes.items():
-            if attribute not in telemetry["attributes"]:
-                telemetry["attributes"][attribute] = value
+            if attribute not in attributes:
+                attributes[attribute] = value
 
     def _apply_user_attributes_to_telemetry(
-        self, telemetry: "Union[Log, Metric]"
+        self, telemetry: "Union[Log, Metric, StreamedSpan]"
     ) -> None:
-        attributes = telemetry["attributes"]
+        if isinstance(telemetry, dict):
+            attributes = telemetry["attributes"]
+        else:
+            attributes = telemetry._attributes
 
         if not should_send_default_pii() or self._user is None:
             return
@@ -1625,20 +1673,22 @@ def apply_to_event(
         return event
 
     @_disable_capture
-    def apply_to_telemetry(self, telemetry: "Union[Log, Metric]") -> None:
+    def apply_to_telemetry(self, telemetry: "Union[Log, Metric, StreamedSpan]") -> None:
         # Attributes-based events and telemetry go through here (logs, metrics,
         # spansV2)
-        trace_context = self.get_trace_context()
-        trace_id = trace_context.get("trace_id")
-        if telemetry.get("trace_id") is None:
-            telemetry["trace_id"] = trace_id or "00000000-0000-0000-0000-000000000000"
-        span_id = trace_context.get("span_id")
-        if telemetry.get("span_id") is None and span_id:
-            telemetry["span_id"] = span_id
+        if not isinstance(telemetry, StreamedSpan):
+            trace_context = self.get_trace_context()
+            trace_id = trace_context.get("trace_id")
+            if telemetry.get("trace_id") is None:
+                telemetry["trace_id"] = (
+                    trace_id or "00000000-0000-0000-0000-000000000000"
+                )
+            span_id = trace_context.get("span_id")
+            if telemetry.get("span_id") is None and span_id:
+                telemetry["span_id"] = span_id
 
         self._apply_scope_attributes_to_telemetry(telemetry)
         self._apply_user_attributes_to_telemetry(telemetry)
-        self._apply_global_attributes_to_telemetry(telemetry)
 
     def update_from_scope(self, scope: "Scope") -> None:
         """Update the scope with another scope's data."""
@@ -1668,6 +1718,8 @@ def update_from_scope(self, scope: "Scope") -> None:
             self._gen_ai_original_message_count.update(
                 scope._gen_ai_original_message_count
             )
+        if scope._gen_ai_conversation_id:
+            self._gen_ai_conversation_id = scope._gen_ai_conversation_id
         if scope._span:
             self._span = scope._span
         if scope._attachments:
diff --git a/sentry_sdk/traces.py b/sentry_sdk/traces.py
new file mode 100644
index 0000000000..a63a9bebb0
--- /dev/null
+++ b/sentry_sdk/traces.py
@@ -0,0 +1,70 @@
+"""
+The API in this file is only meant to be used in span streaming mode.
+
+You can enable span streaming mode via
+sentry_sdk.init(_experiments={"trace_lifecycle": "stream"}).
+"""
+
+import uuid
+from typing import TYPE_CHECKING
+
+from sentry_sdk.utils import format_attribute
+
+if TYPE_CHECKING:
+    from typing import Optional
+    from sentry_sdk._types import Attributes, AttributeValue
+
+
+class StreamedSpan:
+    """
+    A span holds timing information of a block of code.
+
+    Spans can have multiple child spans thus forming a span tree.
+
+    This is the Span First span implementation. The original transaction-based
+    span implementation lives in tracing.Span.
+    """
+
+    __slots__ = (
+        "name",
+        "_attributes",
+        "_trace_id",
+    )
+
+    def __init__(
+        self,
+        *,
+        name: str,
+        attributes: "Optional[Attributes]" = None,
+        trace_id: "Optional[str]" = None,
+    ):
+        self.name: str = name
+        self._attributes: "Attributes" = {}
+        if attributes:
+            for attribute, value in attributes.items():
+                self.set_attribute(attribute, value)
+
+        self._trace_id = trace_id
+
+    def get_attributes(self) -> "Attributes":
+        return self._attributes
+
+    def set_attribute(self, key: str, value: "AttributeValue") -> None:
+        self._attributes[key] = format_attribute(value)
+
+    def set_attributes(self, attributes: "Attributes") -> None:
+        for key, value in attributes.items():
+            self.set_attribute(key, value)
+
+    def remove_attribute(self, key: str) -> None:
+        try:
+            del self._attributes[key]
+        except KeyError:
+            pass
+
+    @property
+    def trace_id(self) -> str:
+        if not self._trace_id:
+            self._trace_id = uuid.uuid4().hex
+
+        return self._trace_id
diff --git a/sentry_sdk/tracing.py b/sentry_sdk/tracing.py
index c4b38e4528..a778da7361 100644
--- a/sentry_sdk/tracing.py
+++ b/sentry_sdk/tracing.py
@@ -676,6 +676,17 @@ def finish(
             self.timestamp = datetime.now(timezone.utc)
 
         scope = scope or sentry_sdk.get_current_scope()
+
+        # Copy conversation_id from scope to span data if this is an AI span
+        conversation_id = scope.get_conversation_id()
+        if conversation_id:
+            has_ai_op = SPANDATA.GEN_AI_OPERATION_NAME in self._data
+            is_ai_span_op = self.op is not None and (
+                self.op.startswith("ai.") or self.op.startswith("gen_ai.")
+            )
+            if has_ai_op or is_ai_span_op:
+                self.set_data("gen_ai.conversation.id", conversation_id)
+
         maybe_create_breadcrumbs_from_span(scope, self)
 
         return None
diff --git a/sentry_sdk/tracing_utils.py b/sentry_sdk/tracing_utils.py
index f45b849499..c1d6c44535 100644
--- a/sentry_sdk/tracing_utils.py
+++ b/sentry_sdk/tracing_utils.py
@@ -4,7 +4,7 @@
 import os
 import re
 import sys
-from collections.abc import Mapping
+from collections.abc import Mapping, MutableMapping
 from datetime import timedelta
 from random import Random
 from urllib.parse import quote, unquote
@@ -106,6 +106,13 @@ def has_tracing_enabled(options: "Optional[Dict[str, Any]]") -> bool:
     )
 
 
+def has_span_streaming_enabled(options: "Optional[dict[str, Any]]") -> bool:
+    if options is None:
+        return False
+
+    return (options.get("_experiments") or {}).get("trace_lifecycle") == "stream"
+
+
 @contextlib.contextmanager
 def record_sql_queries(
     cursor: "Any",
@@ -1285,6 +1292,25 @@ def _should_continue_trace(baggage: "Optional[Baggage]") -> bool:
     return True
 
 
+def add_sentry_baggage_to_headers(
+    headers: "MutableMapping[str, str]", sentry_baggage: str
+) -> None:
+    """Add the Sentry baggage to the headers.
+
+    This function directly mutates the provided headers. The provided sentry_baggage
+    is appended to the existing baggage. If the baggage already contains Sentry items,
+    they are stripped out first.
+    """
+    existing_baggage = headers.get(BAGGAGE_HEADER_NAME, "")
+    stripped_existing_baggage = Baggage.strip_sentry_baggage(existing_baggage)
+
+    separator = "," if len(stripped_existing_baggage) > 0 else ""
+
+    headers[BAGGAGE_HEADER_NAME] = (
+        stripped_existing_baggage + separator + sentry_baggage
+    )
+
+
 # Circular imports
 from sentry_sdk.tracing import (
     BAGGAGE_HEADER_NAME,
diff --git a/sentry_sdk/transport.py b/sentry_sdk/transport.py
index cee4fa882b..dcfe55406b 100644
--- a/sentry_sdk/transport.py
+++ b/sentry_sdk/transport.py
@@ -340,7 +340,21 @@ def record_loss(reason: str) -> None:
         try:
             self._update_rate_limits(response)
 
-            if response.status == 429:
+            if response.status == 413:
+                size_exceeded_message = (
+                    "HTTP 413: Event dropped due to exceeded envelope size limit"
+                )
+                response_message = getattr(
+                    response, "data", getattr(response, "content", None)
+                )
+                if response_message is not None:
+                    size_exceeded_message += f" (body: {response_message})"
+
+                logger.error(size_exceeded_message)
+                self.on_dropped_event("status_413")
+                record_loss("send_error")
+
+            elif response.status == 429:
                 # if we hit a 429.  Something was rate limited but we already
                 # acted on this in `self._update_rate_limits`.  Note that we
                 # do not want to record event loss here as we will have recorded
diff --git a/sentry_sdk/utils.py b/sentry_sdk/utils.py
index c99b81a2f5..2fbca486de 100644
--- a/sentry_sdk/utils.py
+++ b/sentry_sdk/utils.py
@@ -4,6 +4,7 @@
 import logging
 import math
 import os
+import copy
 import random
 import re
 import subprocess
@@ -2061,6 +2062,25 @@ def format_attribute(val: "Any") -> "AttributeValue":
     if isinstance(val, (bool, int, float, str)):
         return val
 
+    # Only lists of elements of a single type are supported
+    list_types: 'dict[type, Literal["string[]", "integer[]", "double[]", "boolean[]"]]' = {
+        str: "string[]",
+        int: "integer[]",
+        float: "double[]",
+        bool: "boolean[]",
+    }
+
+    if isinstance(val, (list, tuple)) and not val:
+        return []
+    elif isinstance(val, list):
+        ty = type(val[0])
+        if ty in list_types and all(type(v) is ty for v in val):
+            return copy.deepcopy(val)
+    elif isinstance(val, tuple):
+        ty = type(val[0])
+        if ty in list_types and all(type(v) is ty for v in val):
+            return list(val)
+
     return safe_repr(val)
 
 
@@ -2075,6 +2095,22 @@ def serialize_attribute(val: "AttributeValue") -> "SerializedAttributeValue":
     if isinstance(val, str):
         return {"value": val, "type": "string"}
 
+    if isinstance(val, list):
+        if not val:
+            return {"value": [], "type": "string[]"}
+
+        # Only lists of elements of a single type are supported
+        list_types: 'dict[type, Literal["string[]", "integer[]", "double[]", "boolean[]"]]' = {
+            str: "string[]",
+            int: "integer[]",
+            float: "double[]",
+            bool: "boolean[]",
+        }
+
+        ty = type(val[0])
+        if ty in list_types and all(type(v) is ty for v in val):
+            return {"value": val, "type": list_types[ty]}
+
     # Coerce to string if we don't know what to do with the value. This should
     # never happen as we pre-format early in format_attribute, but let's be safe.
     return {"value": safe_repr(val), "type": "string"}
diff --git a/setup.py b/setup.py
index a76dbc00d0..ef682c95b3 100644
--- a/setup.py
+++ b/setup.py
@@ -21,7 +21,7 @@ def get_file_text(file_name):
 
 setup(
     name="sentry-sdk",
-    version="2.48.0",
+    version="2.51.0",
     author="Sentry Team and Contributors",
     author_email="hello@sentry.io",
     url="https://github.com/getsentry/sentry-python",
diff --git a/tests/conftest.py b/tests/conftest.py
index dea36f8bda..1cf29bf977 100644
--- a/tests/conftest.py
+++ b/tests/conftest.py
@@ -1,5 +1,7 @@
 import json
 import os
+import asyncio
+from urllib.parse import urlparse, parse_qs
 import socket
 import warnings
 import brotli
@@ -16,6 +18,12 @@
 from werkzeug.wrappers import Request, Response
 import jsonschema
 
+try:
+    from starlette.testclient import TestClient
+    # Catch RuntimeError to prevent the following exception in aws_lambda tests.
+    # RuntimeError: The starlette.testclient module requires the httpx package to be installed.
+except (ImportError, RuntimeError):
+    TestClient = None
 
 try:
     import gevent
@@ -45,9 +53,40 @@
 from typing import TYPE_CHECKING
 
 if TYPE_CHECKING:
-    from typing import Optional
+    from typing import Any, Callable, MutableMapping, Optional
     from collections.abc import Iterator
 
+try:
+    from anyio import create_memory_object_stream, create_task_group, EndOfStream
+    from mcp.types import (
+        JSONRPCMessage,
+        JSONRPCNotification,
+        JSONRPCRequest,
+    )
+    from mcp.shared.message import SessionMessage
+    from httpx import (
+        ASGITransport,
+        Request as HttpxRequest,
+        Response as HttpxResponse,
+        AsyncByteStream,
+        AsyncClient,
+    )
+except ImportError:
+    create_memory_object_stream = None
+    create_task_group = None
+    EndOfStream = None
+
+    JSONRPCMessage = None
+    JSONRPCNotification = None
+    JSONRPCRequest = None
+    SessionMessage = None
+
+    ASGITransport = None
+    HttpxRequest = None
+    HttpxResponse = None
+    AsyncByteStream = None
+    AsyncClient = None
+
 
 SENTRY_EVENT_SCHEMA = "./checkouts/data-schemas/relay/event.schema.json"
 
@@ -592,6 +631,363 @@ def suppress_deprecation_warnings():
         yield
 
 
+@pytest.fixture
+def get_initialization_payload():
+    def inner(request_id: str):
+        return SessionMessage(  # type: ignore
+            message=JSONRPCMessage(  # type: ignore
+                root=JSONRPCRequest(  # type: ignore
+                    jsonrpc="2.0",
+                    id=request_id,
+                    method="initialize",
+                    params={
+                        "protocolVersion": "2025-11-25",
+                        "capabilities": {},
+                        "clientInfo": {"name": "test-client", "version": "1.0.0"},
+                    },
+                )
+            )
+        )
+
+    return inner
+
+
+@pytest.fixture
+def get_initialized_notification_payload():
+    def inner():
+        return SessionMessage(  # type: ignore
+            message=JSONRPCMessage(  # type: ignore
+                root=JSONRPCNotification(  # type: ignore
+                    jsonrpc="2.0",
+                    method="notifications/initialized",
+                )
+            )
+        )
+
+    return inner
+
+
+@pytest.fixture
+def get_mcp_command_payload():
+    def inner(method: str, params, request_id: str):
+        return SessionMessage(  # type: ignore
+            message=JSONRPCMessage(  # type: ignore
+                root=JSONRPCRequest(  # type: ignore
+                    jsonrpc="2.0",
+                    id=request_id,
+                    method=method,
+                    params=params,
+                )
+            )
+        )
+
+    return inner
+
+
+@pytest.fixture
+def stdio(
+    get_initialization_payload,
+    get_initialized_notification_payload,
+    get_mcp_command_payload,
+):
+    async def inner(server, method: str, params, request_id: str | None = None):
+        if request_id is None:
+            request_id = "1"
+
+        read_stream_writer, read_stream = create_memory_object_stream(0)  # type: ignore
+        write_stream, write_stream_reader = create_memory_object_stream(0)  # type: ignore
+
+        result = {}
+
+        async def run_server():
+            await server.run(
+                read_stream, write_stream, server.create_initialization_options()
+            )
+
+        async def simulate_client(tg, result):
+            init_request = get_initialization_payload("1")
+            await read_stream_writer.send(init_request)
+
+            await write_stream_reader.receive()
+
+            initialized_notification = get_initialized_notification_payload()
+            await read_stream_writer.send(initialized_notification)
+
+            request = get_mcp_command_payload(
+                method, params=params, request_id=request_id
+            )
+            await read_stream_writer.send(request)
+
+            result["response"] = await write_stream_reader.receive()
+
+            tg.cancel_scope.cancel()
+
+        async with create_task_group() as tg:  # type: ignore
+            tg.start_soon(run_server)
+            tg.start_soon(simulate_client, tg, result)
+
+        return result["response"]
+
+    return inner
+
+
+@pytest.fixture()
+def json_rpc():
+    def inner(app, method: str, params, request_id: str):
+        with TestClient(app) as client:  # type: ignore
+            init_response = client.post(
+                "/mcp/",
+                headers={
+                    "Accept": "application/json, text/event-stream",
+                    "Content-Type": "application/json",
+                },
+                json={
+                    "jsonrpc": "2.0",
+                    "method": "initialize",
+                    "params": {
+                        "clientInfo": {"name": "test-client", "version": "1.0"},
+                        "protocolVersion": "2025-11-25",
+                        "capabilities": {},
+                    },
+                    "id": request_id,
+                },
+            )
+
+            session_id = init_response.headers["mcp-session-id"]
+
+            # Notification response is mandatory.
+            # https://modelcontextprotocol.io/specification/2025-11-25/basic/lifecycle
+            client.post(
+                "/mcp/",
+                headers={
+                    "Accept": "application/json, text/event-stream",
+                    "Content-Type": "application/json",
+                    "mcp-session-id": session_id,
+                },
+                json={
+                    "jsonrpc": "2.0",
+                    "method": "notifications/initialized",
+                    "params": {},
+                },
+            )
+
+            response = client.post(
+                "/mcp/",
+                headers={
+                    "Accept": "application/json, text/event-stream",
+                    "Content-Type": "application/json",
+                    "mcp-session-id": session_id,
+                },
+                json={
+                    "jsonrpc": "2.0",
+                    "method": method,
+                    "params": params,
+                    "id": request_id,
+                },
+            )
+
+            return session_id, response
+
+    return inner
+
+
+@pytest.fixture()
+def select_mcp_transactions():
+    def inner(events):
+        return [
+            event
+            for event in events
+            if event["type"] == "transaction"
+            and event["contexts"]["trace"]["op"] == "mcp.server"
+        ]
+
+    return inner
+
+
+@pytest.fixture()
+def json_rpc_sse():
+    class StreamingASGITransport(ASGITransport):
+        """
+        Simple transport whose only purpose is to keep GET request alive in SSE connections, allowing
+        tests involving SSE interactions to run in-process.
+        """
+
+        def __init__(
+            self,
+            app: "Callable",
+            keep_sse_alive: "asyncio.Event",
+        ) -> None:
+            self.keep_sse_alive = keep_sse_alive
+            super().__init__(app)
+
+        async def handle_async_request(
+            self, request: "HttpxRequest"
+        ) -> "HttpxResponse":
+            scope = {
+                "type": "http",
+                "method": request.method,
+                "headers": [(k.lower(), v) for (k, v) in request.headers.raw],
+                "path": request.url.path,
+                "query_string": request.url.query,
+            }
+
+            is_streaming_sse = scope["method"] == "GET" and scope["path"] == "/sse"
+            if not is_streaming_sse:
+                return await super().handle_async_request(request)
+
+            request_body = b""
+            if request.content:
+                request_body = await request.aread()
+
+            body_sender, body_receiver = create_memory_object_stream[bytes](0)  # type: ignore
+
+            async def receive() -> "dict[str, Any]":
+                if self.keep_sse_alive.is_set():
+                    return {"type": "http.disconnect"}
+
+                await self.keep_sse_alive.wait()  # Keep alive :)
+                return {
+                    "type": "http.request",
+                    "body": request_body,
+                    "more_body": False,
+                }
+
+            async def send(message: "MutableMapping[str, Any]") -> None:
+                if message["type"] == "http.response.body":
+                    body = message.get("body", b"")
+                    more_body = message.get("more_body", False)
+
+                    if body == b"" and not more_body:
+                        return
+
+                    if body:
+                        await body_sender.send(body)
+
+                    if not more_body:
+                        await body_sender.aclose()
+
+            async def run_app():
+                await self.app(scope, receive, send)
+
+            class StreamingBodyStream(AsyncByteStream):  # type: ignore
+                def __init__(self, receiver):
+                    self.receiver = receiver
+
+                async def __aiter__(self):
+                    try:
+                        async for chunk in self.receiver:
+                            yield chunk
+                    except EndOfStream:  # type: ignore
+                        pass
+
+            stream = StreamingBodyStream(body_receiver)
+            response = HttpxResponse(status_code=200, headers=[], stream=stream)  # type: ignore
+
+            asyncio.create_task(run_app())
+            return response
+
+    def parse_sse_data_package(sse_chunk):
+        sse_text = sse_chunk.decode("utf-8")
+        json_str = sse_text.split("data: ")[1]
+        return json.loads(json_str)
+
+    async def inner(
+        app, method: str, params, request_id: str, keep_sse_alive: "asyncio.Event"
+    ):
+        context = {}
+
+        stream_complete = asyncio.Event()
+        endpoint_parsed = asyncio.Event()
+
+        # https://github.com/Kludex/starlette/issues/104#issuecomment-729087925
+        async with AsyncClient(  # type: ignore
+            transport=StreamingASGITransport(app=app, keep_sse_alive=keep_sse_alive),
+            base_url="http://test",
+        ) as client:
+
+            async def parse_stream():
+                async with client.stream("GET", "/sse") as stream:
+                    # Read directly from stream.stream instead of aiter_bytes()
+                    async for chunk in stream.stream:
+                        if b"event: endpoint" in chunk:
+                            sse_text = chunk.decode("utf-8")
+                            url = sse_text.split("data: ")[1]
+
+                            parsed = urlparse(url)
+                            query_params = parse_qs(parsed.query)
+                            context["session_id"] = query_params["session_id"][0]
+                            endpoint_parsed.set()
+                            continue
+
+                        if b"event: message" in chunk and b"structuredContent" in chunk:
+                            context["response"] = parse_sse_data_package(chunk)
+                            break
+                        elif (
+                            "result" in parse_sse_data_package(chunk)
+                            and "content" in parse_sse_data_package(chunk)["result"]
+                        ):
+                            context["response"] = parse_sse_data_package(chunk)
+                            break
+
+                stream_complete.set()
+
+            task = asyncio.create_task(parse_stream())
+            await endpoint_parsed.wait()
+
+            await client.post(
+                f"/messages/?session_id={context['session_id']}",
+                headers={
+                    "Content-Type": "application/json",
+                },
+                json={
+                    "jsonrpc": "2.0",
+                    "method": "initialize",
+                    "params": {
+                        "clientInfo": {"name": "test-client", "version": "1.0"},
+                        "protocolVersion": "2025-11-25",
+                        "capabilities": {},
+                    },
+                    "id": request_id,
+                },
+            )
+
+            # Notification response is mandatory.
+            # https://modelcontextprotocol.io/specification/2025-11-25/basic/lifecycle
+            await client.post(
+                f"/messages/?session_id={context['session_id']}",
+                headers={
+                    "Content-Type": "application/json",
+                    "mcp-session-id": context["session_id"],
+                },
+                json={
+                    "jsonrpc": "2.0",
+                    "method": "notifications/initialized",
+                    "params": {},
+                },
+            )
+
+            await client.post(
+                f"/messages/?session_id={context['session_id']}",
+                headers={
+                    "Content-Type": "application/json",
+                    "mcp-session-id": context["session_id"],
+                },
+                json={
+                    "jsonrpc": "2.0",
+                    "method": method,
+                    "params": params,
+                    "id": request_id,
+                },
+            )
+
+            await stream_complete.wait()
+            keep_sse_alive.set()
+
+            return task, context["session_id"], context["response"]
+
+    return inner
+
+
 class MockServerRequestHandler(BaseHTTPRequestHandler):
     def do_GET(self):  # noqa: N802
         # Process an HTTP GET request and return a response.
diff --git a/tests/integrations/anthropic/test_anthropic.py b/tests/integrations/anthropic/test_anthropic.py
index 2204505d47..84d773e129 100644
--- a/tests/integrations/anthropic/test_anthropic.py
+++ b/tests/integrations/anthropic/test_anthropic.py
@@ -42,12 +42,15 @@ async def __call__(self, *args, **kwargs):
     from anthropic.types.content_block import ContentBlock as TextBlock
 
 from sentry_sdk import start_transaction, start_span
+from sentry_sdk._types import BLOB_DATA_SUBSTITUTE
 from sentry_sdk.consts import OP, SPANDATA
 from sentry_sdk.integrations.anthropic import (
     AnthropicIntegration,
     _set_output_data,
     _collect_ai_data,
+    _transform_anthropic_content_block,
 )
+from sentry_sdk.ai.utils import transform_content_part, transform_message_content
 from sentry_sdk.utils import package_version
 
 
@@ -850,10 +853,11 @@ def test_collect_ai_data_with_input_json_delta():
     output_tokens = 20
     content_blocks = []
 
-    model, new_input_tokens, new_output_tokens, new_content_blocks = _collect_ai_data(
-        event, model, input_tokens, output_tokens, content_blocks
+    model, new_input_tokens, new_output_tokens, _, _, new_content_blocks = (
+        _collect_ai_data(
+            event, model, input_tokens, output_tokens, 0, 0, content_blocks
+        )
     )
-
     assert model is None
     assert new_input_tokens == input_tokens
     assert new_output_tokens == output_tokens
@@ -881,6 +885,8 @@ def test_set_output_data_with_input_json_delta(sentry_init):
             model="",
             input_tokens=10,
             output_tokens=20,
+            cache_read_input_tokens=0,
+            cache_write_input_tokens=0,
             content_blocks=[{"text": "".join(json_deltas), "type": "text"}],
         )
 
@@ -893,7 +899,25 @@ def test_set_output_data_with_input_json_delta(sentry_init):
         assert span._data.get(SPANDATA.GEN_AI_USAGE_TOTAL_TOKENS) == 30
 
 
-def test_anthropic_message_role_mapping(sentry_init, capture_events):
+# Test messages with mixed roles including "ai" that should be mapped to "assistant"
+@pytest.mark.parametrize(
+    "test_message,expected_role",
+    [
+        ({"role": "system", "content": "You are helpful."}, "system"),
+        ({"role": "user", "content": "Hello"}, "user"),
+        (
+            {"role": "ai", "content": "Hi there!"},
+            "assistant",
+        ),  # Should be mapped to "assistant"
+        (
+            {"role": "assistant", "content": "How can I help?"},
+            "assistant",
+        ),  # Should stay "assistant"
+    ],
+)
+def test_anthropic_message_role_mapping(
+    sentry_init, capture_events, test_message, expected_role
+):
     """Test that Anthropic integration properly maps message roles like 'ai' to 'assistant'"""
     sentry_init(
         integrations=[AnthropicIntegration(include_prompts=True)],
@@ -918,13 +942,7 @@ def mock_messages_create(*args, **kwargs):
 
     client.messages._post = mock.Mock(return_value=mock_messages_create())
 
-    # Test messages with mixed roles including "ai" that should be mapped to "assistant"
-    test_messages = [
-        {"role": "system", "content": "You are helpful."},
-        {"role": "user", "content": "Hello"},
-        {"role": "ai", "content": "Hi there!"},  # Should be mapped to "assistant"
-        {"role": "assistant", "content": "How can I help?"},  # Should stay "assistant"
-    ]
+    test_messages = [test_message]
 
     with start_transaction(name="anthropic tx"):
         client.messages.create(
@@ -942,22 +960,7 @@ def mock_messages_create(*args, **kwargs):
     # Parse the stored messages
     stored_messages = json.loads(span["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES])
 
-    # Verify that "ai" role was mapped to "assistant"
-    assert len(stored_messages) == 4
-    assert stored_messages[0]["role"] == "system"
-    assert stored_messages[1]["role"] == "user"
-    assert (
-        stored_messages[2]["role"] == "assistant"
-    )  # "ai" should be mapped to "assistant"
-    assert stored_messages[3]["role"] == "assistant"  # should stay "assistant"
-
-    # Verify content is preserved
-    assert stored_messages[2]["content"] == "Hi there!"
-    assert stored_messages[3]["content"] == "How can I help?"
-
-    # Verify no "ai" roles remain
-    roles = [msg["role"] for msg in stored_messages]
-    assert "ai" not in roles
+    assert stored_messages[0]["role"] == expected_role
 
 
 def test_anthropic_message_truncation(sentry_init, capture_events):
@@ -1004,9 +1007,62 @@ def test_anthropic_message_truncation(sentry_init, capture_events):
 
     parsed_messages = json.loads(messages_data)
     assert isinstance(parsed_messages, list)
-    assert len(parsed_messages) == 2
-    assert "small message 4" in str(parsed_messages[0])
-    assert "small message 5" in str(parsed_messages[1])
+    assert len(parsed_messages) == 1
+    assert "small message 5" in str(parsed_messages[0])
+
+    assert chat_span["data"][SPANDATA.META_GEN_AI_ORIGINAL_INPUT_MESSAGES_LENGTH] == 5
+    assert tx["_meta"]["spans"]["0"]["data"]["gen_ai.request.messages"][""]["len"] == 5
+
+
+@pytest.mark.asyncio
+async def test_anthropic_message_truncation_async(sentry_init, capture_events):
+    """Test that large messages are truncated properly in Anthropic integration."""
+    sentry_init(
+        integrations=[AnthropicIntegration(include_prompts=True)],
+        traces_sample_rate=1.0,
+        send_default_pii=True,
+    )
+    events = capture_events()
+
+    client = AsyncAnthropic(api_key="z")
+    client.messages._post = mock.AsyncMock(return_value=EXAMPLE_MESSAGE)
+
+    large_content = (
+        "This is a very long message that will exceed our size limits. " * 1000
+    )
+    messages = [
+        {"role": "user", "content": "small message 1"},
+        {"role": "assistant", "content": large_content},
+        {"role": "user", "content": large_content},
+        {"role": "assistant", "content": "small message 4"},
+        {"role": "user", "content": "small message 5"},
+    ]
+
+    with start_transaction():
+        await client.messages.create(max_tokens=1024, messages=messages, model="model")
+
+    assert len(events) > 0
+    tx = events[0]
+    assert tx["type"] == "transaction"
+
+    chat_spans = [
+        span for span in tx.get("spans", []) if span.get("op") == OP.GEN_AI_CHAT
+    ]
+    assert len(chat_spans) > 0
+
+    chat_span = chat_spans[0]
+    assert chat_span["data"][SPANDATA.GEN_AI_OPERATION_NAME] == "chat"
+    assert SPANDATA.GEN_AI_REQUEST_MESSAGES in chat_span["data"]
+
+    messages_data = chat_span["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES]
+    assert isinstance(messages_data, str)
+
+    parsed_messages = json.loads(messages_data)
+    assert isinstance(parsed_messages, list)
+    assert len(parsed_messages) == 1
+    assert "small message 5" in str(parsed_messages[0])
+
+    assert chat_span["data"][SPANDATA.META_GEN_AI_ORIGINAL_INPUT_MESSAGES_LENGTH] == 5
     assert tx["_meta"]["spans"]["0"]["data"]["gen_ai.request.messages"][""]["len"] == 5
 
 
@@ -1068,17 +1124,22 @@ def test_nonstreaming_create_message_with_system_prompt(
     assert span["data"][SPANDATA.GEN_AI_REQUEST_MODEL] == "model"
 
     if send_default_pii and include_prompts:
+        assert SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS in span["data"]
+        system_instructions = json.loads(
+            span["data"][SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS]
+        )
+        assert system_instructions == [
+            {"type": "text", "content": "You are a helpful assistant."}
+        ]
+
         assert SPANDATA.GEN_AI_REQUEST_MESSAGES in span["data"]
         stored_messages = json.loads(span["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES])
-        assert len(stored_messages) == 2
-        # System message should be first
-        assert stored_messages[0]["role"] == "system"
-        assert stored_messages[0]["content"] == "You are a helpful assistant."
-        # User message should be second
-        assert stored_messages[1]["role"] == "user"
-        assert stored_messages[1]["content"] == "Hello, Claude"
+        assert len(stored_messages) == 1
+        assert stored_messages[0]["role"] == "user"
+        assert stored_messages[0]["content"] == "Hello, Claude"
         assert span["data"][SPANDATA.GEN_AI_RESPONSE_TEXT] == "Hi, I'm Claude."
     else:
+        assert SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS not in span["data"]
         assert SPANDATA.GEN_AI_REQUEST_MESSAGES not in span["data"]
         assert SPANDATA.GEN_AI_RESPONSE_TEXT not in span["data"]
 
@@ -1147,17 +1208,22 @@ async def test_nonstreaming_create_message_with_system_prompt_async(
     assert span["data"][SPANDATA.GEN_AI_REQUEST_MODEL] == "model"
 
     if send_default_pii and include_prompts:
+        assert SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS in span["data"]
+        system_instructions = json.loads(
+            span["data"][SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS]
+        )
+        assert system_instructions == [
+            {"type": "text", "content": "You are a helpful assistant."}
+        ]
+
         assert SPANDATA.GEN_AI_REQUEST_MESSAGES in span["data"]
         stored_messages = json.loads(span["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES])
-        assert len(stored_messages) == 2
-        # System message should be first
-        assert stored_messages[0]["role"] == "system"
-        assert stored_messages[0]["content"] == "You are a helpful assistant."
-        # User message should be second
-        assert stored_messages[1]["role"] == "user"
-        assert stored_messages[1]["content"] == "Hello, Claude"
+        assert len(stored_messages) == 1
+        assert stored_messages[0]["role"] == "user"
+        assert stored_messages[0]["content"] == "Hello, Claude"
         assert span["data"][SPANDATA.GEN_AI_RESPONSE_TEXT] == "Hi, I'm Claude."
     else:
+        assert SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS not in span["data"]
         assert SPANDATA.GEN_AI_REQUEST_MESSAGES not in span["data"]
         assert SPANDATA.GEN_AI_RESPONSE_TEXT not in span["data"]
 
@@ -1258,18 +1324,23 @@ def test_streaming_create_message_with_system_prompt(
     assert span["data"][SPANDATA.GEN_AI_REQUEST_MODEL] == "model"
 
     if send_default_pii and include_prompts:
+        assert SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS in span["data"]
+        system_instructions = json.loads(
+            span["data"][SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS]
+        )
+        assert system_instructions == [
+            {"type": "text", "content": "You are a helpful assistant."}
+        ]
+
         assert SPANDATA.GEN_AI_REQUEST_MESSAGES in span["data"]
         stored_messages = json.loads(span["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES])
-        assert len(stored_messages) == 2
-        # System message should be first
-        assert stored_messages[0]["role"] == "system"
-        assert stored_messages[0]["content"] == "You are a helpful assistant."
-        # User message should be second
-        assert stored_messages[1]["role"] == "user"
-        assert stored_messages[1]["content"] == "Hello, Claude"
+        assert len(stored_messages) == 1
+        assert stored_messages[0]["role"] == "user"
+        assert stored_messages[0]["content"] == "Hello, Claude"
         assert span["data"][SPANDATA.GEN_AI_RESPONSE_TEXT] == "Hi! I'm Claude!"
 
     else:
+        assert SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS not in span["data"]
         assert SPANDATA.GEN_AI_REQUEST_MESSAGES not in span["data"]
         assert SPANDATA.GEN_AI_RESPONSE_TEXT not in span["data"]
 
@@ -1373,18 +1444,23 @@ async def test_streaming_create_message_with_system_prompt_async(
     assert span["data"][SPANDATA.GEN_AI_REQUEST_MODEL] == "model"
 
     if send_default_pii and include_prompts:
+        assert SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS in span["data"]
+        system_instructions = json.loads(
+            span["data"][SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS]
+        )
+        assert system_instructions == [
+            {"type": "text", "content": "You are a helpful assistant."}
+        ]
+
         assert SPANDATA.GEN_AI_REQUEST_MESSAGES in span["data"]
         stored_messages = json.loads(span["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES])
-        assert len(stored_messages) == 2
-        # System message should be first
-        assert stored_messages[0]["role"] == "system"
-        assert stored_messages[0]["content"] == "You are a helpful assistant."
-        # User message should be second
-        assert stored_messages[1]["role"] == "user"
-        assert stored_messages[1]["content"] == "Hello, Claude"
+        assert len(stored_messages) == 1
+        assert stored_messages[0]["role"] == "user"
+        assert stored_messages[0]["content"] == "Hello, Claude"
         assert span["data"][SPANDATA.GEN_AI_RESPONSE_TEXT] == "Hi! I'm Claude!"
 
     else:
+        assert SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS not in span["data"]
         assert SPANDATA.GEN_AI_REQUEST_MESSAGES not in span["data"]
         assert SPANDATA.GEN_AI_RESPONSE_TEXT not in span["data"]
 
@@ -1431,18 +1507,805 @@ def test_system_prompt_with_complex_structure(sentry_init, capture_events):
     (span,) = event["spans"]
 
     assert span["data"][SPANDATA.GEN_AI_OPERATION_NAME] == "chat"
+
+    assert SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS in span["data"]
+    system_instructions = json.loads(span["data"][SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS])
+
+    # System content should be a list of text blocks
+    assert isinstance(system_instructions, list)
+    assert system_instructions == [
+        {"type": "text", "content": "You are a helpful assistant."},
+        {"type": "text", "content": "Be concise and clear."},
+    ]
+
     assert SPANDATA.GEN_AI_REQUEST_MESSAGES in span["data"]
     stored_messages = json.loads(span["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES])
 
-    # Should have system message first, then user message
-    assert len(stored_messages) == 2
-    assert stored_messages[0]["role"] == "system"
-    # System content should be a list of text blocks
-    assert isinstance(stored_messages[0]["content"], list)
-    assert len(stored_messages[0]["content"]) == 2
-    assert stored_messages[0]["content"][0]["type"] == "text"
-    assert stored_messages[0]["content"][0]["text"] == "You are a helpful assistant."
-    assert stored_messages[0]["content"][1]["type"] == "text"
-    assert stored_messages[0]["content"][1]["text"] == "Be concise and clear."
-    assert stored_messages[1]["role"] == "user"
-    assert stored_messages[1]["content"] == "Hello"
+    assert len(stored_messages) == 1
+    assert stored_messages[0]["role"] == "user"
+    assert stored_messages[0]["content"] == "Hello"
+
+
+# Tests for transform_content_part (shared) and _transform_anthropic_content_block helper functions
+
+
+def test_transform_content_part_anthropic_base64_image():
+    """Test that base64 encoded images are transformed to blob format."""
+    content_block = {
+        "type": "image",
+        "source": {
+            "type": "base64",
+            "media_type": "image/jpeg",
+            "data": "base64encodeddata...",
+        },
+    }
+
+    result = transform_content_part(content_block)
+
+    assert result == {
+        "type": "blob",
+        "modality": "image",
+        "mime_type": "image/jpeg",
+        "content": "base64encodeddata...",
+    }
+
+
+def test_transform_content_part_anthropic_url_image():
+    """Test that URL-referenced images are transformed to uri format."""
+    content_block = {
+        "type": "image",
+        "source": {
+            "type": "url",
+            "url": "https://example.com/image.jpg",
+        },
+    }
+
+    result = transform_content_part(content_block)
+
+    assert result == {
+        "type": "uri",
+        "modality": "image",
+        "mime_type": "",
+        "uri": "https://example.com/image.jpg",
+    }
+
+
+def test_transform_content_part_anthropic_file_image():
+    """Test that file_id-referenced images are transformed to file format."""
+    content_block = {
+        "type": "image",
+        "source": {
+            "type": "file",
+            "file_id": "file_abc123",
+        },
+    }
+
+    result = transform_content_part(content_block)
+
+    assert result == {
+        "type": "file",
+        "modality": "image",
+        "mime_type": "",
+        "file_id": "file_abc123",
+    }
+
+
+def test_transform_content_part_anthropic_base64_document():
+    """Test that base64 encoded PDFs are transformed to blob format."""
+    content_block = {
+        "type": "document",
+        "source": {
+            "type": "base64",
+            "media_type": "application/pdf",
+            "data": "base64encodedpdfdata...",
+        },
+    }
+
+    result = transform_content_part(content_block)
+
+    assert result == {
+        "type": "blob",
+        "modality": "document",
+        "mime_type": "application/pdf",
+        "content": "base64encodedpdfdata...",
+    }
+
+
+def test_transform_content_part_anthropic_url_document():
+    """Test that URL-referenced documents are transformed to uri format."""
+    content_block = {
+        "type": "document",
+        "source": {
+            "type": "url",
+            "url": "https://example.com/document.pdf",
+        },
+    }
+
+    result = transform_content_part(content_block)
+
+    assert result == {
+        "type": "uri",
+        "modality": "document",
+        "mime_type": "",
+        "uri": "https://example.com/document.pdf",
+    }
+
+
+def test_transform_content_part_anthropic_file_document():
+    """Test that file_id-referenced documents are transformed to file format."""
+    content_block = {
+        "type": "document",
+        "source": {
+            "type": "file",
+            "file_id": "file_doc456",
+            "media_type": "application/pdf",
+        },
+    }
+
+    result = transform_content_part(content_block)
+
+    assert result == {
+        "type": "file",
+        "modality": "document",
+        "mime_type": "application/pdf",
+        "file_id": "file_doc456",
+    }
+
+
+def test_transform_anthropic_content_block_text_document():
+    """Test that plain text documents are transformed correctly (Anthropic-specific)."""
+    content_block = {
+        "type": "document",
+        "source": {
+            "type": "text",
+            "media_type": "text/plain",
+            "data": "This is plain text content.",
+        },
+    }
+
+    # Use Anthropic-specific helper for text-type documents
+    result = _transform_anthropic_content_block(content_block)
+
+    assert result == {
+        "type": "text",
+        "text": "This is plain text content.",
+    }
+
+
+def test_transform_content_part_text_block():
+    """Test that regular text blocks return None (not transformed)."""
+    content_block = {
+        "type": "text",
+        "text": "Hello, world!",
+    }
+
+    # Shared transform_content_part returns None for text blocks
+    result = transform_content_part(content_block)
+
+    assert result is None
+
+
+def test_transform_message_content_string():
+    """Test that string content is returned as-is."""
+    result = transform_message_content("Hello, world!")
+    assert result == "Hello, world!"
+
+
+def test_transform_message_content_list_anthropic():
+    """Test that list content with Anthropic format is transformed correctly."""
+    content = [
+        {"type": "text", "text": "Hello!"},
+        {
+            "type": "image",
+            "source": {
+                "type": "base64",
+                "media_type": "image/png",
+                "data": "base64data...",
+            },
+        },
+    ]
+
+    result = transform_message_content(content)
+
+    assert len(result) == 2
+    # Text block stays as-is (transform returns None, keeps original)
+    assert result[0] == {"type": "text", "text": "Hello!"}
+    assert result[1] == {
+        "type": "blob",
+        "modality": "image",
+        "mime_type": "image/png",
+        "content": "base64data...",
+    }
+
+
+# Integration tests for binary data in messages
+
+
+def test_message_with_base64_image(sentry_init, capture_events):
+    """Test that messages with base64 images are properly captured."""
+    sentry_init(
+        integrations=[AnthropicIntegration(include_prompts=True)],
+        traces_sample_rate=1.0,
+        send_default_pii=True,
+    )
+    events = capture_events()
+    client = Anthropic(api_key="z")
+    client.messages._post = mock.Mock(return_value=EXAMPLE_MESSAGE)
+
+    messages = [
+        {
+            "role": "user",
+            "content": [
+                {"type": "text", "text": "What's in this image?"},
+                {
+                    "type": "image",
+                    "source": {
+                        "type": "base64",
+                        "media_type": "image/jpeg",
+                        "data": "base64encodeddatahere...",
+                    },
+                },
+            ],
+        }
+    ]
+
+    with start_transaction(name="anthropic"):
+        client.messages.create(max_tokens=1024, messages=messages, model="model")
+
+    assert len(events) == 1
+    (event,) = events
+    (span,) = event["spans"]
+
+    assert SPANDATA.GEN_AI_REQUEST_MESSAGES in span["data"]
+    stored_messages = json.loads(span["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES])
+
+    assert len(stored_messages) == 1
+    assert stored_messages[0]["role"] == "user"
+    content = stored_messages[0]["content"]
+    assert len(content) == 2
+    assert content[0] == {"type": "text", "text": "What's in this image?"}
+    assert content[1] == {
+        "type": "blob",
+        "modality": "image",
+        "mime_type": "image/jpeg",
+        "content": BLOB_DATA_SUBSTITUTE,
+    }
+
+
+def test_message_with_url_image(sentry_init, capture_events):
+    """Test that messages with URL-referenced images are properly captured."""
+    sentry_init(
+        integrations=[AnthropicIntegration(include_prompts=True)],
+        traces_sample_rate=1.0,
+        send_default_pii=True,
+    )
+    events = capture_events()
+    client = Anthropic(api_key="z")
+    client.messages._post = mock.Mock(return_value=EXAMPLE_MESSAGE)
+
+    messages = [
+        {
+            "role": "user",
+            "content": [
+                {"type": "text", "text": "Describe this image."},
+                {
+                    "type": "image",
+                    "source": {
+                        "type": "url",
+                        "url": "https://example.com/photo.png",
+                    },
+                },
+            ],
+        }
+    ]
+
+    with start_transaction(name="anthropic"):
+        client.messages.create(max_tokens=1024, messages=messages, model="model")
+
+    assert len(events) == 1
+    (event,) = events
+    (span,) = event["spans"]
+
+    stored_messages = json.loads(span["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES])
+    content = stored_messages[0]["content"]
+    assert content[1] == {
+        "type": "uri",
+        "modality": "image",
+        "mime_type": "",
+        "uri": "https://example.com/photo.png",
+    }
+
+
+def test_message_with_file_image(sentry_init, capture_events):
+    """Test that messages with file_id-referenced images are properly captured."""
+    sentry_init(
+        integrations=[AnthropicIntegration(include_prompts=True)],
+        traces_sample_rate=1.0,
+        send_default_pii=True,
+    )
+    events = capture_events()
+    client = Anthropic(api_key="z")
+    client.messages._post = mock.Mock(return_value=EXAMPLE_MESSAGE)
+
+    messages = [
+        {
+            "role": "user",
+            "content": [
+                {"type": "text", "text": "What do you see?"},
+                {
+                    "type": "image",
+                    "source": {
+                        "type": "file",
+                        "file_id": "file_img_12345",
+                        "media_type": "image/webp",
+                    },
+                },
+            ],
+        }
+    ]
+
+    with start_transaction(name="anthropic"):
+        client.messages.create(max_tokens=1024, messages=messages, model="model")
+
+    assert len(events) == 1
+    (event,) = events
+    (span,) = event["spans"]
+
+    stored_messages = json.loads(span["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES])
+    content = stored_messages[0]["content"]
+    assert content[1] == {
+        "type": "file",
+        "modality": "image",
+        "mime_type": "image/webp",
+        "file_id": "file_img_12345",
+    }
+
+
+def test_message_with_base64_pdf(sentry_init, capture_events):
+    """Test that messages with base64-encoded PDF documents are properly captured."""
+    sentry_init(
+        integrations=[AnthropicIntegration(include_prompts=True)],
+        traces_sample_rate=1.0,
+        send_default_pii=True,
+    )
+    events = capture_events()
+    client = Anthropic(api_key="z")
+    client.messages._post = mock.Mock(return_value=EXAMPLE_MESSAGE)
+
+    messages = [
+        {
+            "role": "user",
+            "content": [
+                {"type": "text", "text": "Summarize this document."},
+                {
+                    "type": "document",
+                    "source": {
+                        "type": "base64",
+                        "media_type": "application/pdf",
+                        "data": "JVBERi0xLjQKJeLj...base64pdfdata",
+                    },
+                },
+            ],
+        }
+    ]
+
+    with start_transaction(name="anthropic"):
+        client.messages.create(max_tokens=1024, messages=messages, model="model")
+
+    assert len(events) == 1
+    (event,) = events
+    (span,) = event["spans"]
+
+    stored_messages = json.loads(span["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES])
+    content = stored_messages[0]["content"]
+    assert content[1] == {
+        "type": "blob",
+        "modality": "document",
+        "mime_type": "application/pdf",
+        "content": BLOB_DATA_SUBSTITUTE,
+    }
+
+
+def test_message_with_url_pdf(sentry_init, capture_events):
+    """Test that messages with URL-referenced PDF documents are properly captured."""
+    sentry_init(
+        integrations=[AnthropicIntegration(include_prompts=True)],
+        traces_sample_rate=1.0,
+        send_default_pii=True,
+    )
+    events = capture_events()
+    client = Anthropic(api_key="z")
+    client.messages._post = mock.Mock(return_value=EXAMPLE_MESSAGE)
+
+    messages = [
+        {
+            "role": "user",
+            "content": [
+                {"type": "text", "text": "What is in this PDF?"},
+                {
+                    "type": "document",
+                    "source": {
+                        "type": "url",
+                        "url": "https://example.com/report.pdf",
+                    },
+                },
+            ],
+        }
+    ]
+
+    with start_transaction(name="anthropic"):
+        client.messages.create(max_tokens=1024, messages=messages, model="model")
+
+    assert len(events) == 1
+    (event,) = events
+    (span,) = event["spans"]
+
+    stored_messages = json.loads(span["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES])
+    content = stored_messages[0]["content"]
+    assert content[1] == {
+        "type": "uri",
+        "modality": "document",
+        "mime_type": "",
+        "uri": "https://example.com/report.pdf",
+    }
+
+
+def test_message_with_file_document(sentry_init, capture_events):
+    """Test that messages with file_id-referenced documents are properly captured."""
+    sentry_init(
+        integrations=[AnthropicIntegration(include_prompts=True)],
+        traces_sample_rate=1.0,
+        send_default_pii=True,
+    )
+    events = capture_events()
+    client = Anthropic(api_key="z")
+    client.messages._post = mock.Mock(return_value=EXAMPLE_MESSAGE)
+
+    messages = [
+        {
+            "role": "user",
+            "content": [
+                {"type": "text", "text": "Analyze this document."},
+                {
+                    "type": "document",
+                    "source": {
+                        "type": "file",
+                        "file_id": "file_doc_67890",
+                        "media_type": "application/pdf",
+                    },
+                },
+            ],
+        }
+    ]
+
+    with start_transaction(name="anthropic"):
+        client.messages.create(max_tokens=1024, messages=messages, model="model")
+
+    assert len(events) == 1
+    (event,) = events
+    (span,) = event["spans"]
+
+    stored_messages = json.loads(span["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES])
+    content = stored_messages[0]["content"]
+    assert content[1] == {
+        "type": "file",
+        "modality": "document",
+        "mime_type": "application/pdf",
+        "file_id": "file_doc_67890",
+    }
+
+
+def test_message_with_mixed_content(sentry_init, capture_events):
+    """Test that messages with mixed content (text, images, documents) are properly captured."""
+    sentry_init(
+        integrations=[AnthropicIntegration(include_prompts=True)],
+        traces_sample_rate=1.0,
+        send_default_pii=True,
+    )
+    events = capture_events()
+    client = Anthropic(api_key="z")
+    client.messages._post = mock.Mock(return_value=EXAMPLE_MESSAGE)
+
+    messages = [
+        {
+            "role": "user",
+            "content": [
+                {"type": "text", "text": "Compare this image with the document."},
+                {
+                    "type": "image",
+                    "source": {
+                        "type": "base64",
+                        "media_type": "image/png",
+                        "data": "iVBORw0KGgo...base64imagedata",
+                    },
+                },
+                {
+                    "type": "image",
+                    "source": {
+                        "type": "url",
+                        "url": "https://example.com/comparison.jpg",
+                    },
+                },
+                {
+                    "type": "document",
+                    "source": {
+                        "type": "base64",
+                        "media_type": "application/pdf",
+                        "data": "JVBERi0xLjQK...base64pdfdata",
+                    },
+                },
+                {"type": "text", "text": "Please provide a detailed analysis."},
+            ],
+        }
+    ]
+
+    with start_transaction(name="anthropic"):
+        client.messages.create(max_tokens=1024, messages=messages, model="model")
+
+    assert len(events) == 1
+    (event,) = events
+    (span,) = event["spans"]
+
+    stored_messages = json.loads(span["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES])
+    content = stored_messages[0]["content"]
+
+    assert len(content) == 5
+    assert content[0] == {
+        "type": "text",
+        "text": "Compare this image with the document.",
+    }
+    assert content[1] == {
+        "type": "blob",
+        "modality": "image",
+        "mime_type": "image/png",
+        "content": BLOB_DATA_SUBSTITUTE,
+    }
+    assert content[2] == {
+        "type": "uri",
+        "modality": "image",
+        "mime_type": "",
+        "uri": "https://example.com/comparison.jpg",
+    }
+    assert content[3] == {
+        "type": "blob",
+        "modality": "document",
+        "mime_type": "application/pdf",
+        "content": BLOB_DATA_SUBSTITUTE,
+    }
+    assert content[4] == {
+        "type": "text",
+        "text": "Please provide a detailed analysis.",
+    }
+
+
+def test_message_with_multiple_images_different_formats(sentry_init, capture_events):
+    """Test that messages with multiple images of different source types are handled."""
+    sentry_init(
+        integrations=[AnthropicIntegration(include_prompts=True)],
+        traces_sample_rate=1.0,
+        send_default_pii=True,
+    )
+    events = capture_events()
+    client = Anthropic(api_key="z")
+    client.messages._post = mock.Mock(return_value=EXAMPLE_MESSAGE)
+
+    messages = [
+        {
+            "role": "user",
+            "content": [
+                {
+                    "type": "image",
+                    "source": {
+                        "type": "base64",
+                        "media_type": "image/jpeg",
+                        "data": "base64data1...",
+                    },
+                },
+                {
+                    "type": "image",
+                    "source": {
+                        "type": "url",
+                        "url": "https://example.com/img2.gif",
+                    },
+                },
+                {
+                    "type": "image",
+                    "source": {
+                        "type": "file",
+                        "file_id": "file_img_789",
+                        "media_type": "image/webp",
+                    },
+                },
+                {"type": "text", "text": "Compare these three images."},
+            ],
+        }
+    ]
+
+    with start_transaction(name="anthropic"):
+        client.messages.create(max_tokens=1024, messages=messages, model="model")
+
+    assert len(events) == 1
+    (event,) = events
+    (span,) = event["spans"]
+
+    stored_messages = json.loads(span["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES])
+    content = stored_messages[0]["content"]
+
+    assert len(content) == 4
+    assert content[0] == {
+        "type": "blob",
+        "modality": "image",
+        "mime_type": "image/jpeg",
+        "content": BLOB_DATA_SUBSTITUTE,
+    }
+    assert content[1] == {
+        "type": "uri",
+        "modality": "image",
+        "mime_type": "",
+        "uri": "https://example.com/img2.gif",
+    }
+    assert content[2] == {
+        "type": "file",
+        "modality": "image",
+        "mime_type": "image/webp",
+        "file_id": "file_img_789",
+    }
+    assert content[3] == {"type": "text", "text": "Compare these three images."}
+
+
+def test_binary_content_not_stored_when_pii_disabled(sentry_init, capture_events):
+    """Test that binary content is not stored when send_default_pii is False."""
+    sentry_init(
+        integrations=[AnthropicIntegration(include_prompts=True)],
+        traces_sample_rate=1.0,
+        send_default_pii=False,
+    )
+    events = capture_events()
+    client = Anthropic(api_key="z")
+    client.messages._post = mock.Mock(return_value=EXAMPLE_MESSAGE)
+
+    messages = [
+        {
+            "role": "user",
+            "content": [
+                {"type": "text", "text": "What's in this image?"},
+                {
+                    "type": "image",
+                    "source": {
+                        "type": "base64",
+                        "media_type": "image/jpeg",
+                        "data": "base64encodeddatahere...",
+                    },
+                },
+            ],
+        }
+    ]
+
+    with start_transaction(name="anthropic"):
+        client.messages.create(max_tokens=1024, messages=messages, model="model")
+
+    assert len(events) == 1
+    (event,) = events
+    (span,) = event["spans"]
+
+    # Messages should not be stored
+    assert SPANDATA.GEN_AI_REQUEST_MESSAGES not in span["data"]
+
+
+def test_binary_content_not_stored_when_prompts_disabled(sentry_init, capture_events):
+    """Test that binary content is not stored when include_prompts is False."""
+    sentry_init(
+        integrations=[AnthropicIntegration(include_prompts=False)],
+        traces_sample_rate=1.0,
+        send_default_pii=True,
+    )
+    events = capture_events()
+    client = Anthropic(api_key="z")
+    client.messages._post = mock.Mock(return_value=EXAMPLE_MESSAGE)
+
+    messages = [
+        {
+            "role": "user",
+            "content": [
+                {"type": "text", "text": "What's in this image?"},
+                {
+                    "type": "image",
+                    "source": {
+                        "type": "base64",
+                        "media_type": "image/jpeg",
+                        "data": "base64encodeddatahere...",
+                    },
+                },
+            ],
+        }
+    ]
+
+    with start_transaction(name="anthropic"):
+        client.messages.create(max_tokens=1024, messages=messages, model="model")
+
+    assert len(events) == 1
+    (event,) = events
+    (span,) = event["spans"]
+
+    # Messages should not be stored
+    assert SPANDATA.GEN_AI_REQUEST_MESSAGES not in span["data"]
+
+
+def test_cache_tokens_nonstreaming(sentry_init, capture_events):
+    """Test cache read/write tokens are tracked for non-streaming responses."""
+    sentry_init(integrations=[AnthropicIntegration()], traces_sample_rate=1.0)
+    events = capture_events()
+    client = Anthropic(api_key="z")
+
+    client.messages._post = mock.Mock(
+        return_value=Message(
+            id="id",
+            model="claude-3-5-sonnet-20241022",
+            role="assistant",
+            content=[TextBlock(type="text", text="Response")],
+            type="message",
+            usage=Usage(
+                input_tokens=100,
+                output_tokens=50,
+                cache_read_input_tokens=80,
+                cache_creation_input_tokens=20,
+            ),
+        )
+    )
+
+    with start_transaction(name="anthropic"):
+        client.messages.create(
+            max_tokens=1024,
+            messages=[{"role": "user", "content": "Hello"}],
+            model="claude-3-5-sonnet-20241022",
+        )
+
+    (span,) = events[0]["spans"]
+    assert span["data"][SPANDATA.GEN_AI_USAGE_INPUT_TOKENS_CACHED] == 80
+    assert span["data"][SPANDATA.GEN_AI_USAGE_INPUT_TOKENS_CACHE_WRITE] == 20
+
+
+def test_cache_tokens_streaming(sentry_init, capture_events):
+    """Test cache tokens are tracked for streaming responses."""
+    client = Anthropic(api_key="z")
+    returned_stream = Stream(cast_to=None, response=None, client=client)
+    returned_stream._iterator = [
+        MessageStartEvent(
+            type="message_start",
+            message=Message(
+                id="id",
+                model="claude-3-5-sonnet-20241022",
+                role="assistant",
+                content=[],
+                type="message",
+                usage=Usage(
+                    input_tokens=100,
+                    output_tokens=0,
+                    cache_read_input_tokens=80,
+                    cache_creation_input_tokens=20,
+                ),
+            ),
+        ),
+        MessageDeltaEvent(
+            type="message_delta",
+            delta=Delta(stop_reason="end_turn"),
+            usage=MessageDeltaUsage(output_tokens=10),
+        ),
+    ]
+
+    sentry_init(integrations=[AnthropicIntegration()], traces_sample_rate=1.0)
+    events = capture_events()
+    client.messages._post = mock.Mock(return_value=returned_stream)
+
+    with start_transaction(name="anthropic"):
+        for _ in client.messages.create(
+            max_tokens=1024,
+            messages=[{"role": "user", "content": "Hello"}],
+            model="claude-3-5-sonnet-20241022",
+            stream=True,
+        ):
+            pass
+
+    (span,) = events[0]["spans"]
+    assert span["data"][SPANDATA.GEN_AI_USAGE_INPUT_TOKENS_CACHED] == 80
+    assert span["data"][SPANDATA.GEN_AI_USAGE_INPUT_TOKENS_CACHE_WRITE] == 20
diff --git a/tests/integrations/arq/test_arq.py b/tests/integrations/arq/test_arq.py
index d8b7e715f2..177f047101 100644
--- a/tests/integrations/arq/test_arq.py
+++ b/tests/integrations/arq/test_arq.py
@@ -131,9 +131,58 @@ def inner(
     return inner
 
 
+@pytest.fixture
+def init_arq_with_kwarg_settings(sentry_init):
+    """Test fixture that passes settings_cls as keyword argument only."""
+
+    def inner(
+        cls_functions=None,
+        cls_cron_jobs=None,
+        kw_functions=None,
+        kw_cron_jobs=None,
+        allow_abort_jobs_=False,
+    ):
+        cls_functions = cls_functions or []
+        cls_cron_jobs = cls_cron_jobs or []
+
+        kwargs = {}
+        if kw_functions is not None:
+            kwargs["functions"] = kw_functions
+        if kw_cron_jobs is not None:
+            kwargs["cron_jobs"] = kw_cron_jobs
+
+        sentry_init(
+            integrations=[ArqIntegration()],
+            traces_sample_rate=1.0,
+            send_default_pii=True,
+        )
+
+        server = FakeRedis()
+        pool = ArqRedis(pool_or_conn=server.connection_pool)
+
+        class WorkerSettings:
+            functions = cls_functions
+            cron_jobs = cls_cron_jobs
+            redis_pool = pool
+            allow_abort_jobs = allow_abort_jobs_
+
+        if not WorkerSettings.functions:
+            del WorkerSettings.functions
+        if not WorkerSettings.cron_jobs:
+            del WorkerSettings.cron_jobs
+
+        # Pass settings_cls as keyword argument (not positional)
+        worker = arq.worker.create_worker(settings_cls=WorkerSettings, **kwargs)
+
+        return pool, worker
+
+    return inner
+
+
 @pytest.mark.asyncio
 @pytest.mark.parametrize(
-    "init_arq_settings", ["init_arq", "init_arq_with_dict_settings"]
+    "init_arq_settings",
+    ["init_arq", "init_arq_with_dict_settings", "init_arq_with_kwarg_settings"],
 )
 async def test_job_result(init_arq_settings, request):
     async def increase(ctx, num):
diff --git a/tests/integrations/asyncio/test_asyncio.py b/tests/integrations/asyncio/test_asyncio.py
index 11b60fb0e1..b41aa244cb 100644
--- a/tests/integrations/asyncio/test_asyncio.py
+++ b/tests/integrations/asyncio/test_asyncio.py
@@ -7,7 +7,11 @@
 
 import sentry_sdk
 from sentry_sdk.consts import OP
-from sentry_sdk.integrations.asyncio import AsyncioIntegration, patch_asyncio
+from sentry_sdk.integrations.asyncio import (
+    AsyncioIntegration,
+    patch_asyncio,
+    enable_asyncio_integration,
+)
 
 try:
     from contextvars import Context, ContextVar
@@ -229,6 +233,7 @@ def test_patch_asyncio(mock_get_running_loop):
     Test that the patch_asyncio function will patch the task factory.
     """
     mock_loop = mock_get_running_loop.return_value
+    mock_loop.get_task_factory.return_value._is_sentry_task_factory = False
 
     patch_asyncio()
 
@@ -278,6 +283,7 @@ def test_sentry_task_factory_with_factory(mock_get_running_loop):
 
     # The original task factory will be mocked out here, let's retrieve the value for later
     orig_task_factory = mock_loop.get_task_factory.return_value
+    orig_task_factory._is_sentry_task_factory = False
 
     # Retieve sentry task factory (since it is an inner function within patch_asyncio)
     sentry_task_factory = get_sentry_task_factory(mock_get_running_loop)
@@ -340,6 +346,7 @@ def test_sentry_task_factory_context_with_factory(mock_get_running_loop):
 
     # The original task factory will be mocked out here, let's retrieve the value for later
     orig_task_factory = mock_loop.get_task_factory.return_value
+    orig_task_factory._is_sentry_task_factory = False
 
     # Retieve sentry task factory (since it is an inner function within patch_asyncio)
     sentry_task_factory = get_sentry_task_factory(mock_get_running_loop)
@@ -386,3 +393,174 @@ async def test_span_origin(
 
     assert event["contexts"]["trace"]["origin"] == "manual"
     assert event["spans"][0]["origin"] == "auto.function.asyncio"
+
+
+@minimum_python_38
+@pytest.mark.asyncio
+async def test_task_spans_false(
+    sentry_init,
+    capture_events,
+    uninstall_integration,
+):
+    uninstall_integration("asyncio")
+
+    sentry_init(
+        traces_sample_rate=1.0,
+        integrations=[
+            AsyncioIntegration(task_spans=False),
+        ],
+    )
+
+    events = capture_events()
+
+    with sentry_sdk.start_transaction(name="test_no_spans"):
+        tasks = [asyncio.create_task(foo()), asyncio.create_task(bar())]
+        await asyncio.wait(tasks, return_when=asyncio.FIRST_EXCEPTION)
+
+    sentry_sdk.flush()
+
+    (transaction_event,) = events
+
+    assert not transaction_event["spans"]
+
+
+@minimum_python_38
+@pytest.mark.asyncio
+async def test_enable_asyncio_integration_with_task_spans_false(
+    sentry_init,
+    capture_events,
+    uninstall_integration,
+):
+    """
+    Test that enable_asyncio_integration() helper works with task_spans=False.
+    """
+    uninstall_integration("asyncio")
+
+    sentry_init(traces_sample_rate=1.0)
+
+    assert "asyncio" not in sentry_sdk.get_client().integrations
+
+    enable_asyncio_integration(task_spans=False)
+
+    assert "asyncio" in sentry_sdk.get_client().integrations
+    assert sentry_sdk.get_client().integrations["asyncio"].task_spans is False
+
+    events = capture_events()
+
+    with sentry_sdk.start_transaction(name="test"):
+        await asyncio.create_task(foo())
+
+    sentry_sdk.flush()
+
+    (transaction,) = events
+    assert not transaction["spans"]
+
+
+@minimum_python_38
+@pytest.mark.asyncio
+async def test_delayed_enable_integration(sentry_init, capture_events):
+    sentry_init(traces_sample_rate=1.0)
+
+    assert "asyncio" not in sentry_sdk.get_client().integrations
+
+    events = capture_events()
+
+    with sentry_sdk.start_transaction(name="test"):
+        await asyncio.create_task(foo())
+
+    assert len(events) == 1
+    (transaction,) = events
+    assert not transaction["spans"]
+
+    enable_asyncio_integration()
+
+    events = capture_events()
+
+    assert "asyncio" in sentry_sdk.get_client().integrations
+
+    with sentry_sdk.start_transaction(name="test"):
+        await asyncio.create_task(foo())
+
+    assert len(events) == 1
+    (transaction,) = events
+    assert transaction["spans"]
+    assert transaction["spans"][0]["origin"] == "auto.function.asyncio"
+
+
+@minimum_python_38
+@pytest.mark.asyncio
+async def test_delayed_enable_integration_with_options(sentry_init, capture_events):
+    sentry_init(traces_sample_rate=1.0)
+
+    assert "asyncio" not in sentry_sdk.get_client().integrations
+
+    mock_init = MagicMock(return_value=None)
+    mock_setup_once = MagicMock()
+    with patch(
+        "sentry_sdk.integrations.asyncio.AsyncioIntegration.__init__", mock_init
+    ):
+        with patch(
+            "sentry_sdk.integrations.asyncio.AsyncioIntegration.setup_once",
+            mock_setup_once,
+        ):
+            enable_asyncio_integration("arg", kwarg="kwarg")
+
+    assert "asyncio" in sentry_sdk.get_client().integrations
+    mock_init.assert_called_once_with("arg", kwarg="kwarg")
+    mock_setup_once.assert_called_once()
+
+
+@minimum_python_38
+@pytest.mark.asyncio
+async def test_delayed_enable_enabled_integration(sentry_init, uninstall_integration):
+    # Ensure asyncio integration is not already installed from previous tests
+    uninstall_integration("asyncio")
+
+    integration = AsyncioIntegration()
+    sentry_init(integrations=[integration], traces_sample_rate=1.0)
+
+    assert "asyncio" in sentry_sdk.get_client().integrations
+
+    # Get the task factory after initial setup - it should be Sentry's
+    loop = asyncio.get_running_loop()
+    task_factory_before = loop.get_task_factory()
+    assert getattr(task_factory_before, "_is_sentry_task_factory", False) is True
+
+    enable_asyncio_integration()
+
+    assert "asyncio" in sentry_sdk.get_client().integrations
+
+    # The task factory should be the same (loop not re-patched)
+    task_factory_after = loop.get_task_factory()
+    assert task_factory_before is task_factory_after
+
+
+@minimum_python_38
+@pytest.mark.asyncio
+async def test_delayed_enable_integration_after_disabling(sentry_init, capture_events):
+    sentry_init(disabled_integrations=[AsyncioIntegration()], traces_sample_rate=1.0)
+
+    assert "asyncio" not in sentry_sdk.get_client().integrations
+
+    events = capture_events()
+
+    with sentry_sdk.start_transaction(name="test"):
+        await asyncio.create_task(foo())
+
+    assert len(events) == 1
+    (transaction,) = events
+    assert not transaction["spans"]
+
+    enable_asyncio_integration()
+
+    events = capture_events()
+
+    assert "asyncio" in sentry_sdk.get_client().integrations
+
+    with sentry_sdk.start_transaction(name="test"):
+        await asyncio.create_task(foo())
+
+    assert len(events) == 1
+    (transaction,) = events
+    assert transaction["spans"]
+    assert transaction["spans"][0]["origin"] == "auto.function.asyncio"
diff --git a/tests/integrations/dramatiq/test_dramatiq.py b/tests/integrations/dramatiq/test_dramatiq.py
index 3860ee61d9..a9d3966839 100644
--- a/tests/integrations/dramatiq/test_dramatiq.py
+++ b/tests/integrations/dramatiq/test_dramatiq.py
@@ -1,15 +1,16 @@
-import pytest
 import uuid
 
 import dramatiq
+import pytest
 from dramatiq.brokers.stub import StubBroker
+from dramatiq.middleware import Middleware, SkipMessage
 
 import sentry_sdk
-from sentry_sdk.tracing import TransactionSource
 from sentry_sdk import start_transaction
 from sentry_sdk.consts import SPANSTATUS
 from sentry_sdk.integrations.dramatiq import DramatiqIntegration
 from sentry_sdk.integrations.logging import ignore_logger
+from sentry_sdk.tracing import Transaction, TransactionSource
 
 ignore_logger("dramatiq.worker.WorkerThread")
 
@@ -386,3 +387,28 @@ def dummy_actor():
     worker.join()
 
     assert events == []
+
+
+@pytest.mark.parametrize("broker", [1.0], indirect=True)
+def test_that_skip_message_cleans_up_scope_and_transaction(
+    broker, worker, capture_events
+):
+    transactions: list[Transaction] = []
+
+    class SkipMessageMiddleware(Middleware):
+        def before_process_message(self, broker, message):
+            transactions.append(sentry_sdk.get_current_scope().transaction)
+            raise SkipMessage()
+
+    broker.add_middleware(SkipMessageMiddleware())
+
+    @dramatiq.actor(max_retries=0)
+    def skipped_actor(): ...
+
+    skipped_actor.send()
+
+    broker.join(skipped_actor.queue_name)
+    worker.join()
+
+    (transaction,) = transactions
+    assert transaction.timestamp is not None
diff --git a/tests/integrations/fastmcp/test_fastmcp.py b/tests/integrations/fastmcp/test_fastmcp.py
index ef2a1f9cb7..d32747855a 100644
--- a/tests/integrations/fastmcp/test_fastmcp.py
+++ b/tests/integrations/fastmcp/test_fastmcp.py
@@ -21,6 +21,7 @@
 accurate testing of the integration's behavior in real MCP Server scenarios.
 """
 
+import anyio
 import asyncio
 import json
 import pytest
@@ -39,6 +40,19 @@ async def __call__(self, *args, **kwargs):
 from sentry_sdk.consts import SPANDATA, OP
 from sentry_sdk.integrations.mcp import MCPIntegration
 
+from mcp.server.sse import SseServerTransport
+from mcp.server.streamable_http_manager import StreamableHTTPSessionManager
+
+try:
+    from fastmcp.prompts import Message
+except ImportError:
+    Message = None
+
+
+from starlette.responses import Response
+from starlette.routing import Mount, Route
+from starlette.applications import Starlette
+
 # Try to import both FastMCP implementations
 try:
     from mcp.server.fastmcp import FastMCP as MCPFastMCP
@@ -71,6 +85,10 @@ async def __call__(self, *args, **kwargs):
     GetPromptRequest = None
     ReadResourceRequest = None
 
+try:
+    from fastmcp import __version__ as FASTMCP_VERSION
+except ImportError:
+    FASTMCP_VERSION = None
 
 # Collect available FastMCP implementations for parametrization
 fastmcp_implementations = []
@@ -245,46 +263,19 @@ def reset_request_ctx():
             pass
 
 
-class MockRequestContext:
-    """Mock MCP request context"""
-
-    def __init__(self, request_id=None, session_id=None, transport="stdio"):
-        self.request_id = request_id
-        if transport in ("http", "sse"):
-            self.request = MockHTTPRequest(session_id, transport)
-        else:
-            self.request = None
-
-
-class MockHTTPRequest:
-    """Mock HTTP request for SSE/StreamableHTTP transport"""
-
-    def __init__(self, session_id=None, transport="http"):
-        self.headers = {}
-        self.query_params = {}
-
-        if transport == "sse":
-            # SSE transport uses query parameter
-            if session_id:
-                self.query_params["session_id"] = session_id
-        else:
-            # StreamableHTTP transport uses header
-            if session_id:
-                self.headers["mcp-session-id"] = session_id
-
-
 # =============================================================================
 # Tool Handler Tests - Verifying Sentry Integration
 # =============================================================================
 
 
+@pytest.mark.asyncio
 @pytest.mark.parametrize("FastMCP", fastmcp_implementations, ids=fastmcp_ids)
 @pytest.mark.parametrize(
     "send_default_pii, include_prompts",
     [(True, True), (True, False), (False, True), (False, False)],
 )
-def test_fastmcp_tool_sync(
-    sentry_init, capture_events, FastMCP, send_default_pii, include_prompts
+async def test_fastmcp_tool_sync(
+    sentry_init, capture_events, FastMCP, send_default_pii, include_prompts, stdio
 ):
     """Test that FastMCP synchronous tool handlers create proper spans"""
     sentry_init(
@@ -296,11 +287,6 @@ def test_fastmcp_tool_sync(
 
     mcp = FastMCP("Test Server")
 
-    # Set up mock request context
-    if request_ctx is not None:
-        mock_ctx = MockRequestContext(request_id="req-123", transport="stdio")
-        request_ctx.set(mock_ctx)
-
     @mcp.tool()
     def add_numbers(a: int, b: int) -> dict:
         """Add two numbers together"""
@@ -308,9 +294,20 @@ def add_numbers(a: int, b: int) -> dict:
 
     with start_transaction(name="fastmcp tx"):
         # Call through MCP protocol to trigger instrumentation
-        result = call_tool_through_mcp(mcp, "add_numbers", {"a": 10, "b": 5})
+        result = await stdio(
+            mcp._mcp_server,
+            method="tools/call",
+            params={
+                "name": "add_numbers",
+                "arguments": {"a": 10, "b": 5},
+            },
+            request_id="req-123",
+        )
 
-    assert result == {"result": 15, "operation": "addition"}
+    assert json.loads(result.message.root.result["content"][0]["text"]) == {
+        "result": 15,
+        "operation": "addition",
+    }
 
     (tx,) = events
     assert tx["type"] == "transaction"
@@ -340,7 +337,13 @@ def add_numbers(a: int, b: int) -> dict:
     [(True, True), (True, False), (False, True), (False, False)],
 )
 async def test_fastmcp_tool_async(
-    sentry_init, capture_events, FastMCP, send_default_pii, include_prompts
+    sentry_init,
+    capture_events,
+    FastMCP,
+    send_default_pii,
+    include_prompts,
+    json_rpc,
+    select_mcp_transactions,
 ):
     """Test that FastMCP async tool handlers create proper spans"""
     sentry_init(
@@ -352,49 +355,61 @@ async def test_fastmcp_tool_async(
 
     mcp = FastMCP("Test Server")
 
-    # Set up mock request context
-    if request_ctx is not None:
-        mock_ctx = MockRequestContext(
-            request_id="req-456", session_id="session-789", transport="http"
-        )
-        request_ctx.set(mock_ctx)
+    session_manager = StreamableHTTPSessionManager(
+        app=mcp._mcp_server,
+        json_response=True,
+    )
+
+    app = Starlette(
+        routes=[
+            Mount("/mcp", app=session_manager.handle_request),
+        ],
+        lifespan=lambda app: session_manager.run(),
+    )
 
     @mcp.tool()
     async def multiply_numbers(x: int, y: int) -> dict:
         """Multiply two numbers together"""
         return {"result": x * y, "operation": "multiplication"}
 
-    with start_transaction(name="fastmcp tx"):
-        result = await call_tool_through_mcp_async(
-            mcp, "multiply_numbers", {"x": 7, "y": 6}
-        )
+    session_id, result = json_rpc(
+        app,
+        method="tools/call",
+        params={
+            "name": "multiply_numbers",
+            "arguments": {"x": 7, "y": 6},
+        },
+        request_id="req-456",
+    )
 
-    assert result == {"result": 42, "operation": "multiplication"}
+    assert json.loads(result.json()["result"]["content"][0]["text"]) == {
+        "result": 42,
+        "operation": "multiplication",
+    }
 
-    (tx,) = events
-    assert tx["type"] == "transaction"
-    assert len(tx["spans"]) == 1
+    transactions = select_mcp_transactions(events)
+    assert len(transactions) == 1
+    tx = transactions[0]
 
-    # Verify span structure
-    span = tx["spans"][0]
-    assert span["op"] == OP.MCP_SERVER
-    assert span["origin"] == "auto.ai.mcp"
-    assert span["description"] == "tools/call multiply_numbers"
-    assert span["data"][SPANDATA.MCP_TOOL_NAME] == "multiply_numbers"
-    assert span["data"][SPANDATA.MCP_METHOD_NAME] == "tools/call"
-    assert span["data"][SPANDATA.MCP_TRANSPORT] == "http"
-    assert span["data"][SPANDATA.MCP_REQUEST_ID] == "req-456"
-    assert span["data"][SPANDATA.MCP_SESSION_ID] == "session-789"
+    assert tx["contexts"]["trace"]["op"] == OP.MCP_SERVER
+    assert tx["contexts"]["trace"]["origin"] == "auto.ai.mcp"
+    assert tx["transaction"] == "tools/call multiply_numbers"
+    assert tx["contexts"]["trace"]["data"][SPANDATA.MCP_TOOL_NAME] == "multiply_numbers"
+    assert tx["contexts"]["trace"]["data"][SPANDATA.MCP_METHOD_NAME] == "tools/call"
+    assert tx["contexts"]["trace"]["data"][SPANDATA.MCP_TRANSPORT] == "http"
+    assert tx["contexts"]["trace"]["data"][SPANDATA.MCP_REQUEST_ID] == "req-456"
+    assert tx["contexts"]["trace"]["data"][SPANDATA.MCP_SESSION_ID] == session_id
 
     # Check PII-sensitive data
     if send_default_pii and include_prompts:
-        assert SPANDATA.MCP_TOOL_RESULT_CONTENT in span["data"]
+        assert SPANDATA.MCP_TOOL_RESULT_CONTENT in tx["contexts"]["trace"]["data"]
     else:
-        assert SPANDATA.MCP_TOOL_RESULT_CONTENT not in span["data"]
+        assert SPANDATA.MCP_TOOL_RESULT_CONTENT not in tx["contexts"]["trace"]["data"]
 
 
+@pytest.mark.asyncio
 @pytest.mark.parametrize("FastMCP", fastmcp_implementations, ids=fastmcp_ids)
-def test_fastmcp_tool_with_error(sentry_init, capture_events, FastMCP):
+async def test_fastmcp_tool_with_error(sentry_init, capture_events, FastMCP, stdio):
     """Test that FastMCP tool handler errors are captured properly"""
     sentry_init(
         integrations=[MCPIntegration()],
@@ -404,26 +419,23 @@ def test_fastmcp_tool_with_error(sentry_init, capture_events, FastMCP):
 
     mcp = FastMCP("Test Server")
 
-    # Set up mock request context
-    if request_ctx is not None:
-        mock_ctx = MockRequestContext(request_id="req-error", transport="stdio")
-        request_ctx.set(mock_ctx)
-
     @mcp.tool()
     def failing_tool(value: int) -> int:
         """A tool that always fails"""
         raise ValueError("Tool execution failed")
 
     with start_transaction(name="fastmcp tx"):
-        # MCP protocol may raise the error or return it as an error result
-        try:
-            result = call_tool_through_mcp(mcp, "failing_tool", {"value": 42})
-            # If no exception raised, check if result indicates error
-            if hasattr(result, "isError"):
-                assert result.isError is True
-        except ValueError:
-            # Error was raised as expected
-            pass
+        result = await stdio(
+            mcp._mcp_server,
+            method="tools/call",
+            params={
+                "name": "failing_tool",
+                "arguments": {"value": 42},
+            },
+            request_id="req-error",
+        )
+        # If no exception raised, check if result indicates error
+        assert result.message.root.result["isError"] is True
 
     # Should have transaction and error events
     assert len(events) >= 1
@@ -443,8 +455,9 @@ def failing_tool(value: int) -> int:
     assert tool_spans[0]["data"][SPANDATA.MCP_TOOL_RESULT_IS_ERROR] is True
 
 
+@pytest.mark.asyncio
 @pytest.mark.parametrize("FastMCP", fastmcp_implementations, ids=fastmcp_ids)
-def test_fastmcp_multiple_tools(sentry_init, capture_events, FastMCP):
+async def test_fastmcp_multiple_tools(sentry_init, capture_events, FastMCP, stdio):
     """Test that multiple FastMCP tool calls create multiple spans"""
     sentry_init(
         integrations=[MCPIntegration()],
@@ -454,11 +467,6 @@ def test_fastmcp_multiple_tools(sentry_init, capture_events, FastMCP):
 
     mcp = FastMCP("Test Server")
 
-    # Set up mock request context
-    if request_ctx is not None:
-        mock_ctx = MockRequestContext(request_id="req-multi", transport="stdio")
-        request_ctx.set(mock_ctx)
-
     @mcp.tool()
     def tool_one(x: int) -> int:
         """First tool"""
@@ -475,13 +483,43 @@ def tool_three(z: int) -> int:
         return z - 5
 
     with start_transaction(name="fastmcp tx"):
-        result1 = call_tool_through_mcp(mcp, "tool_one", {"x": 5})
-        result2 = call_tool_through_mcp(mcp, "tool_two", {"y": result1["result"]})
-        result3 = call_tool_through_mcp(mcp, "tool_three", {"z": result2["result"]})
+        result1 = await stdio(
+            mcp._mcp_server,
+            method="tools/call",
+            params={
+                "name": "tool_one",
+                "arguments": {"x": 5},
+            },
+            request_id="req-multi",
+        )
+
+        result2 = await stdio(
+            mcp._mcp_server,
+            method="tools/call",
+            params={
+                "name": "tool_two",
+                "arguments": {
+                    "y": int(result1.message.root.result["content"][0]["text"])
+                },
+            },
+            request_id="req-multi",
+        )
+
+        result3 = await stdio(
+            mcp._mcp_server,
+            method="tools/call",
+            params={
+                "name": "tool_three",
+                "arguments": {
+                    "z": int(result2.message.root.result["content"][0]["text"])
+                },
+            },
+            request_id="req-multi",
+        )
 
-    assert result1["result"] == 10
-    assert result2["result"] == 20
-    assert result3["result"] == 15
+    assert result1.message.root.result["content"][0]["text"] == "10"
+    assert result2.message.root.result["content"][0]["text"] == "20"
+    assert result3.message.root.result["content"][0]["text"] == "15"
 
     (tx,) = events
     assert tx["type"] == "transaction"
@@ -494,8 +532,11 @@ def tool_three(z: int) -> int:
     assert tool_spans[2]["data"][SPANDATA.MCP_TOOL_NAME] == "tool_three"
 
 
+@pytest.mark.asyncio
 @pytest.mark.parametrize("FastMCP", fastmcp_implementations, ids=fastmcp_ids)
-def test_fastmcp_tool_with_complex_return(sentry_init, capture_events, FastMCP):
+async def test_fastmcp_tool_with_complex_return(
+    sentry_init, capture_events, FastMCP, stdio
+):
     """Test FastMCP tool with complex nested return value"""
     sentry_init(
         integrations=[MCPIntegration(include_prompts=True)],
@@ -506,11 +547,6 @@ def test_fastmcp_tool_with_complex_return(sentry_init, capture_events, FastMCP):
 
     mcp = FastMCP("Test Server")
 
-    # Set up mock request context
-    if request_ctx is not None:
-        mock_ctx = MockRequestContext(request_id="req-complex", transport="stdio")
-        request_ctx.set(mock_ctx)
-
     @mcp.tool()
     def get_user_data(user_id: int) -> dict:
         """Get complex user data"""
@@ -522,11 +558,22 @@ def get_user_data(user_id: int) -> dict:
         }
 
     with start_transaction(name="fastmcp tx"):
-        result = call_tool_through_mcp(mcp, "get_user_data", {"user_id": 123})
+        result = await stdio(
+            mcp._mcp_server,
+            method="tools/call",
+            params={
+                "name": "get_user_data",
+                "arguments": {"user_id": 123},
+            },
+            request_id="req-complex",
+        )
 
-    assert result["id"] == 123
-    assert result["name"] == "Alice"
-    assert result["nested"]["preferences"]["theme"] == "dark"
+    assert json.loads(result.message.root.result["content"][0]["text"]) == {
+        "id": 123,
+        "name": "Alice",
+        "nested": {"preferences": {"theme": "dark", "notifications": True}},
+        "tags": ["admin", "verified"],
+    }
 
     (tx,) = events
     assert tx["type"] == "transaction"
@@ -545,13 +592,14 @@ def get_user_data(user_id: int) -> dict:
 # =============================================================================
 
 
+@pytest.mark.asyncio
 @pytest.mark.parametrize("FastMCP", fastmcp_implementations, ids=fastmcp_ids)
 @pytest.mark.parametrize(
     "send_default_pii, include_prompts",
     [(True, True), (False, False)],
 )
-def test_fastmcp_prompt_sync(
-    sentry_init, capture_events, FastMCP, send_default_pii, include_prompts
+async def test_fastmcp_prompt_sync(
+    sentry_init, capture_events, FastMCP, send_default_pii, include_prompts, stdio
 ):
     """Test that FastMCP synchronous prompt handlers create proper spans"""
     sentry_init(
@@ -563,60 +611,69 @@ def test_fastmcp_prompt_sync(
 
     mcp = FastMCP("Test Server")
 
-    # Set up mock request context
-    if request_ctx is not None:
-        mock_ctx = MockRequestContext(request_id="req-prompt", transport="stdio")
-        request_ctx.set(mock_ctx)
-
     # Try to register a prompt handler (may not be supported in all versions)
-    try:
-        if hasattr(mcp, "prompt"):
-
-            @mcp.prompt()
-            def code_help_prompt(language: str):
-                """Get help for a programming language"""
-                return [
-                    {
-                        "role": "user",
-                        "content": {
-                            "type": "text",
-                            "text": f"Tell me about {language}",
-                        },
-                    }
-                ]
-
-            with start_transaction(name="fastmcp tx"):
-                result = call_prompt_through_mcp(
-                    mcp, "code_help_prompt", {"language": "python"}
-                )
+    if hasattr(mcp, "prompt"):
+
+        @mcp.prompt()
+        def code_help_prompt(language: str):
+            """Get help for a programming language"""
+            message = {
+                "role": "user",
+                "content": {
+                    "type": "text",
+                    "text": f"Tell me about {language}",
+                },
+            }
+
+            if FASTMCP_VERSION is not None and FASTMCP_VERSION.startswith("3"):
+                message = Message(message)
+
+            return [message]
+
+        with start_transaction(name="fastmcp tx"):
+            result = await stdio(
+                mcp._mcp_server,
+                method="prompts/get",
+                params={
+                    "name": "code_help_prompt",
+                    "arguments": {"language": "python"},
+                },
+                request_id="req-prompt",
+            )
+
+        assert result.message.root.result["messages"][0]["role"] == "user"
+        assert (
+            "python"
+            in result.message.root.result["messages"][0]["content"]["text"].lower()
+        )
 
-            assert result.messages[0].role == "user"
-            assert "python" in result.messages[0].content.text.lower()
+        (tx,) = events
+        assert tx["type"] == "transaction"
 
-            (tx,) = events
-            assert tx["type"] == "transaction"
+        # Verify prompt span was created
+        prompt_spans = [s for s in tx["spans"] if s["op"] == OP.MCP_SERVER]
+        assert len(prompt_spans) == 1
+        span = prompt_spans[0]
+        assert span["origin"] == "auto.ai.mcp"
+        assert span["description"] == "prompts/get code_help_prompt"
+        assert span["data"][SPANDATA.MCP_PROMPT_NAME] == "code_help_prompt"
 
-            # Verify prompt span was created
-            prompt_spans = [s for s in tx["spans"] if s["op"] == OP.MCP_SERVER]
-            assert len(prompt_spans) == 1
-            span = prompt_spans[0]
-            assert span["origin"] == "auto.ai.mcp"
-            assert span["description"] == "prompts/get code_help_prompt"
-            assert span["data"][SPANDATA.MCP_PROMPT_NAME] == "code_help_prompt"
-
-            # Check PII-sensitive data
-            if send_default_pii and include_prompts:
-                assert SPANDATA.MCP_PROMPT_CONTENT in span["data"]
-            else:
-                assert SPANDATA.MCP_PROMPT_CONTENT not in span["data"]
-    except AttributeError:
-        # Prompt handler not supported in this version
-        pytest.skip("Prompt handlers not supported in this FastMCP version")
+        # Check PII-sensitive data
+        if send_default_pii and include_prompts:
+            assert SPANDATA.MCP_PROMPT_RESULT_MESSAGE_CONTENT in span["data"]
+        else:
+            assert SPANDATA.MCP_PROMPT_RESULT_MESSAGE_CONTENT not in span["data"]
 
 
 @pytest.mark.parametrize("FastMCP", fastmcp_implementations, ids=fastmcp_ids)
 @pytest.mark.asyncio
-async def test_fastmcp_prompt_async(sentry_init, capture_events, FastMCP):
+async def test_fastmcp_prompt_async(
+    sentry_init,
+    capture_events,
+    FastMCP,
+    json_rpc,
+    select_mcp_transactions,
+):
     """Test that FastMCP async prompt handlers create proper spans"""
     sentry_init(
         integrations=[MCPIntegration()],
@@ -626,46 +683,57 @@ async def test_fastmcp_prompt_async(sentry_init, capture_events, FastMCP):
 
     mcp = FastMCP("Test Server")
 
-    # Set up mock request context
-    if request_ctx is not None:
-        mock_ctx = MockRequestContext(
-            request_id="req-async-prompt", session_id="session-abc", transport="http"
-        )
-        request_ctx.set(mock_ctx)
+    session_manager = StreamableHTTPSessionManager(
+        app=mcp._mcp_server,
+        json_response=True,
+    )
 
-    # Try to register an async prompt handler
-    try:
-        if hasattr(mcp, "prompt"):
-
-            @mcp.prompt()
-            async def async_prompt(topic: str):
-                """Get async prompt for a topic"""
-                return [
-                    {
-                        "role": "user",
-                        "content": {"type": "text", "text": f"What is {topic}?"},
-                    },
-                    {
-                        "role": "assistant",
-                        "content": {
-                            "type": "text",
-                            "text": "Let me explain that",
-                        },
-                    },
-                ]
+    app = Starlette(
+        routes=[
+            Mount("/mcp", app=session_manager.handle_request),
+        ],
+        lifespan=lambda app: session_manager.run(),
+    )
 
-            with start_transaction(name="fastmcp tx"):
-                result = await call_prompt_through_mcp_async(
-                    mcp, "async_prompt", {"topic": "MCP"}
-                )
+    # Try to register an async prompt handler
+    if hasattr(mcp, "prompt"):
+
+        @mcp.prompt()
+        async def async_prompt(topic: str):
+            """Get async prompt for a topic"""
+            message1 = {
+                "role": "user",
+                "content": {"type": "text", "text": f"What is {topic}?"},
+            }
+
+            message2 = {
+                "role": "assistant",
+                "content": {
+                    "type": "text",
+                    "text": "Let me explain that",
+                },
+            }
+
+            if FASTMCP_VERSION is not None and FASTMCP_VERSION.startswith("3"):
+                message1 = Message(message1)
+                message2 = Message(message2)
+
+            return [message1, message2]
+
+        _, result = json_rpc(
+            app,
+            method="prompts/get",
+            params={
+                "name": "async_prompt",
+                "arguments": {"topic": "MCP"},
+            },
+            request_id="req-async-prompt",
+        )
 
-            assert len(result.messages) == 2
+        assert len(result.json()["result"]["messages"]) == 2
 
-            (tx,) = events
-            assert tx["type"] == "transaction"
-    except AttributeError:
-        # Prompt handler not supported in this version
-        pytest.skip("Prompt handlers not supported in this FastMCP version")
+        transactions = select_mcp_transactions(events)
+        assert len(transactions) == 1
 
 
 # =============================================================================
@@ -673,8 +741,9 @@ async def async_prompt(topic: str):
 # =============================================================================
 
 
+@pytest.mark.asyncio
 @pytest.mark.parametrize("FastMCP", fastmcp_implementations, ids=fastmcp_ids)
-def test_fastmcp_resource_sync(sentry_init, capture_events, FastMCP):
+async def test_fastmcp_resource_sync(sentry_init, capture_events, FastMCP, stdio):
     """Test that FastMCP synchronous resource handlers create proper spans"""
     sentry_init(
         integrations=[MCPIntegration()],
@@ -684,11 +753,6 @@ def test_fastmcp_resource_sync(sentry_init, capture_events, FastMCP):
 
     mcp = FastMCP("Test Server")
 
-    # Set up mock request context
-    if request_ctx is not None:
-        mock_ctx = MockRequestContext(request_id="req-resource", transport="stdio")
-        request_ctx.set(mock_ctx)
-
     # Try to register a resource handler
     try:
         if hasattr(mcp, "resource"):
@@ -700,7 +764,14 @@ def read_file(path: str):
 
             with start_transaction(name="fastmcp tx"):
                 try:
-                    result = call_resource_through_mcp(mcp, "file:///test.txt")
+                    result = await stdio(
+                        mcp._mcp_server,
+                        method="resources/read",
+                        params={
+                            "uri": "file:///test.txt",
+                        },
+                        request_id="req-resource",
+                    )
                 except ValueError as e:
                     # Older FastMCP versions may not support this URI pattern
                     if "Unknown resource" in str(e):
@@ -710,7 +781,7 @@ def read_file(path: str):
                     raise
 
             # Resource content is returned as-is
-            assert "file contents" in result.contents[0].text
+            assert "file contents" in result.message.root.result["contents"][0]["text"]
 
             (tx,) = events
             assert tx["type"] == "transaction"
@@ -729,7 +800,13 @@ def read_file(path: str):
 
 @pytest.mark.parametrize("FastMCP", fastmcp_implementations, ids=fastmcp_ids)
 @pytest.mark.asyncio
-async def test_fastmcp_resource_async(sentry_init, capture_events, FastMCP):
+async def test_fastmcp_resource_async(
+    sentry_init,
+    capture_events,
+    FastMCP,
+    json_rpc,
+    select_mcp_transactions,
+):
     """Test that FastMCP async resource handlers create proper spans"""
     sentry_init(
         integrations=[MCPIntegration()],
@@ -739,12 +816,17 @@ async def test_fastmcp_resource_async(sentry_init, capture_events, FastMCP):
 
     mcp = FastMCP("Test Server")
 
-    # Set up mock request context
-    if request_ctx is not None:
-        mock_ctx = MockRequestContext(
-            request_id="req-async-resource", session_id="session-res", transport="http"
-        )
-        request_ctx.set(mock_ctx)
+    session_manager = StreamableHTTPSessionManager(
+        app=mcp._mcp_server,
+        json_response=True,
+    )
+
+    app = Starlette(
+        routes=[
+            Mount("/mcp", app=session_manager.handle_request),
+        ],
+        lifespan=lambda app: session_manager.run(),
+    )
 
     # Try to register an async resource handler
     try:
@@ -755,28 +837,31 @@ async def read_url(resource: str):
                 """Read a URL resource"""
                 return "resource data"
 
-            with start_transaction(name="fastmcp tx"):
-                try:
-                    result = await call_resource_through_mcp_async(
-                        mcp, "https://example.com/resource"
-                    )
-                except ValueError as e:
-                    # Older FastMCP versions may not support this URI pattern
-                    if "Unknown resource" in str(e):
-                        pytest.skip(
-                            f"Resource URI not supported in this FastMCP version: {e}"
-                        )
-                    raise
-
-            assert "resource data" in result.contents[0].text
-
-            (tx,) = events
-            assert tx["type"] == "transaction"
-
-            # Verify span was created
-            resource_spans = [s for s in tx["spans"] if s["op"] == OP.MCP_SERVER]
-            assert len(resource_spans) == 1
-            assert resource_spans[0]["data"][SPANDATA.MCP_RESOURCE_PROTOCOL] == "https"
+            _, result = json_rpc(
+                app,
+                method="resources/read",
+                params={
+                    "uri": "https://example.com/resource",
+                },
+                request_id="req-async-resource",
+            )
+            # Older FastMCP versions may not support this URI pattern
+            if (
+                "error" in result.json()
+                and "Unknown resource" in result.json()["error"]["message"]
+            ):
+                pytest.skip("Resource URI not supported in this FastMCP version.")
+                return
+
+            assert "resource data" in result.json()["result"]["contents"][0]["text"]
+
+            transactions = select_mcp_transactions(events)
+            assert len(transactions) == 1
+            tx = transactions[0]
+            assert (
+                tx["contexts"]["trace"]["data"][SPANDATA.MCP_RESOURCE_PROTOCOL]
+                == "https"
+            )
     except (AttributeError, TypeError):
         # Resource handler not supported in this version
         pytest.skip("Resource handlers not supported in this FastMCP version")
@@ -787,8 +872,9 @@ async def read_url(resource: str):
 # =============================================================================
 
 
+@pytest.mark.asyncio
 @pytest.mark.parametrize("FastMCP", fastmcp_implementations, ids=fastmcp_ids)
-def test_fastmcp_span_origin(sentry_init, capture_events, FastMCP):
+async def test_fastmcp_span_origin(sentry_init, capture_events, FastMCP, stdio):
     """Test that FastMCP span origin is set correctly"""
     sentry_init(
         integrations=[MCPIntegration()],
@@ -798,18 +884,21 @@ def test_fastmcp_span_origin(sentry_init, capture_events, FastMCP):
 
     mcp = FastMCP("Test Server")
 
-    # Set up mock request context
-    if request_ctx is not None:
-        mock_ctx = MockRequestContext(request_id="req-origin", transport="stdio")
-        request_ctx.set(mock_ctx)
-
     @mcp.tool()
     def test_tool(value: int) -> int:
         """Test tool for origin checking"""
         return value * 2
 
     with start_transaction(name="fastmcp tx"):
-        call_tool_through_mcp(mcp, "test_tool", {"value": 21})
+        await stdio(
+            mcp._mcp_server,
+            method="tools/call",
+            params={
+                "name": "test_tool",
+                "arguments": {"value": 21},
+            },
+            request_id="req-origin",
+        )
 
     (tx,) = events
 
@@ -821,43 +910,16 @@ def test_tool(value: int) -> int:
     assert mcp_spans[0]["origin"] == "auto.ai.mcp"
 
 
-@pytest.mark.parametrize("FastMCP", fastmcp_implementations, ids=fastmcp_ids)
-def test_fastmcp_without_request_context(sentry_init, capture_events, FastMCP):
-    """Test FastMCP handling when no request context is available"""
-    sentry_init(
-        integrations=[MCPIntegration()],
-        traces_sample_rate=1.0,
-    )
-    events = capture_events()
-
-    mcp = FastMCP("Test Server")
-
-    # Clear request context
-    if request_ctx is not None:
-        request_ctx.set(None)
-
-    @mcp.tool()
-    def test_tool_no_ctx(x: int) -> dict:
-        """Test tool without context"""
-        return {"result": x + 1}
-
-    with start_transaction(name="fastmcp tx"):
-        result = call_tool_through_mcp(mcp, "test_tool_no_ctx", {"x": 99})
-
-    assert result == {"result": 100}
-
-    # Should still create transaction even if context is missing
-    (tx,) = events
-    assert tx["type"] == "transaction"
-
-
 # =============================================================================
 # Transport Detection Tests
 # =============================================================================
 
 
+@pytest.mark.asyncio
 @pytest.mark.parametrize("FastMCP", fastmcp_implementations, ids=fastmcp_ids)
-def test_fastmcp_sse_transport(sentry_init, capture_events, FastMCP):
+async def test_fastmcp_sse_transport(
+    sentry_init, capture_events, FastMCP, json_rpc_sse
+):
     """Test that FastMCP correctly detects SSE transport"""
     sentry_init(
         integrations=[MCPIntegration()],
@@ -866,25 +928,66 @@ def test_fastmcp_sse_transport(sentry_init, capture_events, FastMCP):
     events = capture_events()
 
     mcp = FastMCP("Test Server")
+    sse = SseServerTransport("/messages/")
 
-    # Set up mock request context with SSE transport
-    if request_ctx is not None:
-        mock_ctx = MockRequestContext(
-            request_id="req-sse", session_id="session-sse-123", transport="sse"
-        )
-        request_ctx.set(mock_ctx)
+    sse_connection_closed = asyncio.Event()
+
+    async def handle_sse(request):
+        async with sse.connect_sse(
+            request.scope, request.receive, request._send
+        ) as streams:
+            async with anyio.create_task_group() as tg:
+
+                async def run_server():
+                    await mcp._mcp_server.run(
+                        streams[0],
+                        streams[1],
+                        mcp._mcp_server.create_initialization_options(),
+                    )
+
+                tg.start_soon(run_server)
+
+        sse_connection_closed.set()
+        return Response()
+
+    app = Starlette(
+        routes=[
+            Route("/sse", endpoint=handle_sse, methods=["GET"]),
+            Mount("/messages/", app=sse.handle_post_message),
+        ],
+    )
 
     @mcp.tool()
     def sse_tool(value: str) -> dict:
         """Tool for SSE transport test"""
         return {"message": f"Received: {value}"}
 
-    with start_transaction(name="fastmcp tx"):
-        result = call_tool_through_mcp(mcp, "sse_tool", {"value": "hello"})
+    keep_sse_alive = asyncio.Event()
+    app_task, _, result = await json_rpc_sse(
+        app,
+        method="tools/call",
+        params={
+            "name": "sse_tool",
+            "arguments": {"value": "hello"},
+        },
+        request_id="req-sse",
+        keep_sse_alive=keep_sse_alive,
+    )
 
-    assert result == {"message": "Received: hello"}
+    await sse_connection_closed.wait()
+    await app_task
 
-    (tx,) = events
+    assert json.loads(result["result"]["content"][0]["text"]) == {
+        "message": "Received: hello"
+    }
+
+    transactions = [
+        event
+        for event in events
+        if event["type"] == "transaction" and event["transaction"] == "/sse"
+    ]
+    assert len(transactions) == 1
+    tx = transactions[0]
 
     # Find MCP spans
     mcp_spans = [s for s in tx["spans"] if s["op"] == OP.MCP_SERVER]
@@ -895,7 +998,13 @@ def sse_tool(value: str) -> dict:
 
 
 @pytest.mark.parametrize("FastMCP", fastmcp_implementations, ids=fastmcp_ids)
-def test_fastmcp_http_transport(sentry_init, capture_events, FastMCP):
+def test_fastmcp_http_transport(
+    sentry_init,
+    capture_events,
+    FastMCP,
+    json_rpc,
+    select_mcp_transactions,
+):
     """Test that FastMCP correctly detects HTTP transport"""
     sentry_init(
         integrations=[MCPIntegration()],
@@ -905,35 +1014,48 @@ def test_fastmcp_http_transport(sentry_init, capture_events, FastMCP):
 
     mcp = FastMCP("Test Server")
 
-    # Set up mock request context with HTTP transport
-    if request_ctx is not None:
-        mock_ctx = MockRequestContext(
-            request_id="req-http", session_id="session-http-456", transport="http"
-        )
-        request_ctx.set(mock_ctx)
+    session_manager = StreamableHTTPSessionManager(
+        app=mcp._mcp_server,
+        json_response=True,
+    )
+
+    app = Starlette(
+        routes=[
+            Mount("/mcp", app=session_manager.handle_request),
+        ],
+        lifespan=lambda app: session_manager.run(),
+    )
 
     @mcp.tool()
     def http_tool(data: str) -> dict:
         """Tool for HTTP transport test"""
         return {"processed": data.upper()}
 
-    with start_transaction(name="fastmcp tx"):
-        result = call_tool_through_mcp(mcp, "http_tool", {"data": "test"})
+    _, result = json_rpc(
+        app,
+        method="tools/call",
+        params={
+            "name": "http_tool",
+            "arguments": {"data": "test"},
+        },
+        request_id="req-http",
+    )
 
-    assert result == {"processed": "TEST"}
+    assert json.loads(result.json()["result"]["content"][0]["text"]) == {
+        "processed": "TEST"
+    }
 
-    (tx,) = events
+    transactions = select_mcp_transactions(events)
+    assert len(transactions) == 1
+    tx = transactions[0]
 
-    # Find MCP spans
-    mcp_spans = [s for s in tx["spans"] if s["op"] == OP.MCP_SERVER]
-    assert len(mcp_spans) >= 1
-    span = mcp_spans[0]
     # Check that HTTP transport is detected
-    assert span["data"].get(SPANDATA.MCP_TRANSPORT) == "http"
+    assert tx["contexts"]["trace"]["data"].get(SPANDATA.MCP_TRANSPORT) == "http"
 
 
+@pytest.mark.asyncio
 @pytest.mark.parametrize("FastMCP", fastmcp_implementations, ids=fastmcp_ids)
-def test_fastmcp_stdio_transport(sentry_init, capture_events, FastMCP):
+async def test_fastmcp_stdio_transport(sentry_init, capture_events, FastMCP, stdio):
     """Test that FastMCP correctly detects stdio transport"""
     sentry_init(
         integrations=[MCPIntegration()],
@@ -943,20 +1065,25 @@ def test_fastmcp_stdio_transport(sentry_init, capture_events, FastMCP):
 
     mcp = FastMCP("Test Server")
 
-    # Set up mock request context with stdio transport
-    if request_ctx is not None:
-        mock_ctx = MockRequestContext(request_id="req-stdio", transport="stdio")
-        request_ctx.set(mock_ctx)
-
     @mcp.tool()
     def stdio_tool(n: int) -> dict:
         """Tool for stdio transport test"""
         return {"squared": n * n}
 
     with start_transaction(name="fastmcp tx"):
-        result = call_tool_through_mcp(mcp, "stdio_tool", {"n": 7})
+        result = await stdio(
+            mcp._mcp_server,
+            method="tools/call",
+            params={
+                "name": "stdio_tool",
+                "arguments": {"n": 7},
+            },
+            request_id="req-stdio",
+        )
 
-    assert result == {"squared": 49}
+    assert json.loads(result.message.root.result["content"][0]["text"]) == {
+        "squared": 49
+    }
 
     (tx,) = events
 
@@ -1000,10 +1127,11 @@ def package_specific_tool(x: int) -> int:
     assert tx["type"] == "transaction"
 
 
+@pytest.mark.asyncio
 @pytest.mark.skipif(
     not HAS_STANDALONE_FASTMCP, reason="standalone fastmcp not installed"
 )
-def test_standalone_fastmcp_specific_features(sentry_init, capture_events):
+async def test_standalone_fastmcp_specific_features(sentry_init, capture_events, stdio):
     """Test features specific to standalone fastmcp package"""
     sentry_init(
         integrations=[MCPIntegration()],
@@ -1021,12 +1149,19 @@ def standalone_specific_tool(message: str) -> dict:
         return {"echo": message, "length": len(message)}
 
     with start_transaction(name="standalone fastmcp tx"):
-        result = call_tool_through_mcp(
-            mcp, "standalone_specific_tool", {"message": "Hello FastMCP"}
+        result = await stdio(
+            mcp._mcp_server,
+            method="tools/call",
+            params={
+                "name": "standalone_specific_tool",
+                "arguments": {"message": "Hello FastMCP"},
+            },
         )
 
-    assert result["echo"] == "Hello FastMCP"
-    assert result["length"] == 13
+    assert json.loads(result.message.root.result["content"][0]["text"]) == {
+        "echo": "Hello FastMCP",
+        "length": 13,
+    }
 
     (tx,) = events
     assert tx["type"] == "transaction"
@@ -1037,8 +1172,11 @@ def standalone_specific_tool(message: str) -> dict:
 # =============================================================================
 
 
+@pytest.mark.asyncio
 @pytest.mark.parametrize("FastMCP", fastmcp_implementations, ids=fastmcp_ids)
-def test_fastmcp_tool_with_no_arguments(sentry_init, capture_events, FastMCP):
+async def test_fastmcp_tool_with_no_arguments(
+    sentry_init, capture_events, FastMCP, stdio
+):
     """Test FastMCP tool with no arguments"""
     sentry_init(
         integrations=[MCPIntegration()],
@@ -1054,16 +1192,26 @@ def no_args_tool() -> str:
         return "success"
 
     with start_transaction(name="fastmcp tx"):
-        result = call_tool_through_mcp(mcp, "no_args_tool", {})
+        result = await stdio(
+            mcp._mcp_server,
+            method="tools/call",
+            params={
+                "name": "no_args_tool",
+                "arguments": {},
+            },
+        )
 
-    assert result["result"] == "success"
+    assert result.message.root.result["content"][0]["text"] == "success"
 
     (tx,) = events
     assert tx["type"] == "transaction"
 
 
+@pytest.mark.asyncio
 @pytest.mark.parametrize("FastMCP", fastmcp_implementations, ids=fastmcp_ids)
-def test_fastmcp_tool_with_none_return(sentry_init, capture_events, FastMCP):
+async def test_fastmcp_tool_with_none_return(
+    sentry_init, capture_events, FastMCP, stdio
+):
     """Test FastMCP tool that returns None"""
     sentry_init(
         integrations=[MCPIntegration()],
@@ -1079,18 +1227,33 @@ def none_return_tool(action: str) -> None:
         pass
 
     with start_transaction(name="fastmcp tx"):
-        result = call_tool_through_mcp(mcp, "none_return_tool", {"action": "log"})
+        result = await stdio(
+            mcp._mcp_server,
+            method="tools/call",
+            params={
+                "name": "none_return_tool",
+                "arguments": {"action": "log"},
+            },
+        )
 
-    # Helper function normalizes to {"result": value} format
-    assert result["result"] is None
+    if (
+        isinstance(mcp, StandaloneFastMCP) and FASTMCP_VERSION is not None
+    ) or isinstance(mcp, MCPFastMCP):
+        assert len(result.message.root.result["content"]) == 0
+    else:
+        assert result.message.root.result["content"] == [
+            {"type": "text", "text": "None"}
+        ]
 
     (tx,) = events
     assert tx["type"] == "transaction"
 
 
-@pytest.mark.parametrize("FastMCP", fastmcp_implementations, ids=fastmcp_ids)
 @pytest.mark.asyncio
-async def test_fastmcp_mixed_sync_async_tools(sentry_init, capture_events, FastMCP):
+@pytest.mark.parametrize("FastMCP", fastmcp_implementations, ids=fastmcp_ids)
+async def test_fastmcp_mixed_sync_async_tools(
+    sentry_init, capture_events, FastMCP, stdio
+):
     """Test mixing sync and async tools in FastMCP"""
     sentry_init(
         integrations=[MCPIntegration()],
@@ -1100,11 +1263,6 @@ async def test_fastmcp_mixed_sync_async_tools(sentry_init, capture_events, FastM
 
     mcp = FastMCP("Test Server")
 
-    # Set up mock request context
-    if request_ctx is not None:
-        mock_ctx = MockRequestContext(request_id="req-mixed", transport="stdio")
-        request_ctx.set(mock_ctx)
-
     @mcp.tool()
     def sync_add(a: int, b: int) -> int:
         """Sync addition"""
@@ -1117,13 +1275,27 @@ async def async_multiply(x: int, y: int) -> int:
 
     with start_transaction(name="fastmcp tx"):
         # Use async version for both since we're in an async context
-        result1 = await call_tool_through_mcp_async(mcp, "sync_add", {"a": 3, "b": 4})
-        result2 = await call_tool_through_mcp_async(
-            mcp, "async_multiply", {"x": 5, "y": 6}
+        result1 = await stdio(
+            mcp._mcp_server,
+            method="tools/call",
+            params={
+                "name": "sync_add",
+                "arguments": {"a": 3, "b": 4},
+            },
+            request_id="req-mixed",
+        )
+        result2 = await stdio(
+            mcp._mcp_server,
+            method="tools/call",
+            params={
+                "name": "async_multiply",
+                "arguments": {"x": 5, "y": 6},
+            },
+            request_id="req-mixed",
         )
 
-    assert result1["result"] == 7
-    assert result2["result"] == 30
+    assert result1.message.root.result["content"][0]["text"] == "7"
+    assert result2.message.root.result["content"][0]["text"] == "30"
 
     (tx,) = events
     assert tx["type"] == "transaction"
diff --git a/tests/integrations/google_genai/test_google_genai.py b/tests/integrations/google_genai/test_google_genai.py
index a49822f3d4..37ba50420f 100644
--- a/tests/integrations/google_genai/test_google_genai.py
+++ b/tests/integrations/google_genai/test_google_genai.py
@@ -4,10 +4,13 @@
 
 from google import genai
 from google.genai import types as genai_types
+from google.genai.types import Content, Part
 
 from sentry_sdk import start_transaction
+from sentry_sdk._types import BLOB_DATA_SUBSTITUTE
 from sentry_sdk.consts import OP, SPANDATA
 from sentry_sdk.integrations.google_genai import GoogleGenAIIntegration
+from sentry_sdk.integrations.google_genai.utils import extract_contents_messages
 
 
 @pytest.fixture
@@ -104,11 +107,6 @@ def create_test_config(
     if seed is not None:
         config_dict["seed"] = seed
     if system_instruction is not None:
-        # Convert string to Content for system instruction
-        if isinstance(system_instruction, str):
-            system_instruction = genai_types.Content(
-                parts=[genai_types.Part(text=system_instruction)], role="system"
-            )
         config_dict["system_instruction"] = system_instruction
     if tools is not None:
         config_dict["tools"] = tools
@@ -184,6 +182,7 @@ def test_nonstreaming_generate_content(
         response_texts = json.loads(response_text)
         assert response_texts == ["Hello! How can I help you today?"]
     else:
+        assert SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS not in invoke_span["data"]
         assert SPANDATA.GEN_AI_REQUEST_MESSAGES not in invoke_span["data"]
         assert SPANDATA.GEN_AI_RESPONSE_TEXT not in chat_span["data"]
 
@@ -200,8 +199,41 @@ def test_nonstreaming_generate_content(
     assert invoke_span["data"][SPANDATA.GEN_AI_REQUEST_MAX_TOKENS] == 100
 
 
+@pytest.mark.parametrize("generate_content_config", (False, True))
+@pytest.mark.parametrize(
+    "system_instructions,expected_texts",
+    [
+        (None, None),
+        ({}, []),
+        (Content(role="system", parts=[]), []),
+        ({"parts": []}, []),
+        ("You are a helpful assistant.", ["You are a helpful assistant."]),
+        (Part(text="You are a helpful assistant."), ["You are a helpful assistant."]),
+        (
+            Content(role="system", parts=[Part(text="You are a helpful assistant.")]),
+            ["You are a helpful assistant."],
+        ),
+        ({"text": "You are a helpful assistant."}, ["You are a helpful assistant."]),
+        (
+            {"parts": [Part(text="You are a helpful assistant.")]},
+            ["You are a helpful assistant."],
+        ),
+        (
+            {"parts": [{"text": "You are a helpful assistant."}]},
+            ["You are a helpful assistant."],
+        ),
+        (["You are a helpful assistant."], ["You are a helpful assistant."]),
+        ([Part(text="You are a helpful assistant.")], ["You are a helpful assistant."]),
+        ([{"text": "You are a helpful assistant."}], ["You are a helpful assistant."]),
+    ],
+)
 def test_generate_content_with_system_instruction(
-    sentry_init, capture_events, mock_genai_client
+    sentry_init,
+    capture_events,
+    mock_genai_client,
+    generate_content_config,
+    system_instructions,
+    expected_texts,
 ):
     sentry_init(
         integrations=[GoogleGenAIIntegration(include_prompts=True)],
@@ -216,25 +248,35 @@ def test_generate_content_with_system_instruction(
         mock_genai_client._api_client, "request", return_value=mock_http_response
     ):
         with start_transaction(name="google_genai"):
-            config = create_test_config(
-                system_instruction="You are a helpful assistant",
-                temperature=0.5,
-            )
+            config = {
+                "system_instruction": system_instructions,
+                "temperature": 0.5,
+            }
+
+            if generate_content_config:
+                config = create_test_config(**config)
+
             mock_genai_client.models.generate_content(
-                model="gemini-1.5-flash", contents="What is 2+2?", config=config
+                model="gemini-1.5-flash",
+                contents="What is 2+2?",
+                config=config,
             )
 
     (event,) = events
     invoke_span = event["spans"][0]
 
-    # Check that system instruction is included in messages
+    if expected_texts is None:
+        assert SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS not in invoke_span["data"]
+        return
+
     # (PII is enabled and include_prompts is True in this test)
-    messages_str = invoke_span["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES]
-    # Parse the JSON string to verify content
-    messages = json.loads(messages_str)
-    assert len(messages) == 2
-    assert messages[0] == {"role": "system", "content": "You are a helpful assistant"}
-    assert messages[1] == {"role": "user", "content": "What is 2+2?"}
+    system_instructions = json.loads(
+        invoke_span["data"][SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS]
+    )
+
+    assert system_instructions == [
+        {"type": "text", "content": text} for text in expected_texts
+    ]
 
 
 def test_generate_content_with_tools(sentry_init, capture_events, mock_genai_client):
@@ -931,10 +973,8 @@ def test_google_genai_message_truncation(
         with start_transaction(name="google_genai"):
             mock_genai_client.models.generate_content(
                 model="gemini-1.5-flash",
-                contents=small_content,
-                config=create_test_config(
-                    system_instruction=large_content,
-                ),
+                contents=[large_content, small_content],
+                config=create_test_config(),
             )
 
     (event,) = events
@@ -950,6 +990,7 @@ def test_google_genai_message_truncation(
     assert parsed_messages[0]["role"] == "user"
     assert small_content in parsed_messages[0]["content"]
 
+    assert invoke_span["data"][SPANDATA.META_GEN_AI_ORIGINAL_INPUT_MESSAGES_LENGTH] == 2
     assert (
         event["_meta"]["spans"]["0"]["data"]["gen_ai.request.messages"][""]["len"] == 2
     )
@@ -1417,3 +1458,699 @@ async def test_async_embed_content_span_origin(
     assert event["contexts"]["trace"]["origin"] == "manual"
     for span in event["spans"]:
         assert span["origin"] == "auto.ai.google_genai"
+
+
+# Integration tests for generate_content with different input message formats
+def test_generate_content_with_content_object(
+    sentry_init, capture_events, mock_genai_client
+):
+    """Test generate_content with Content object input."""
+    sentry_init(
+        integrations=[GoogleGenAIIntegration(include_prompts=True)],
+        traces_sample_rate=1.0,
+        send_default_pii=True,
+    )
+    events = capture_events()
+
+    mock_http_response = create_mock_http_response(EXAMPLE_API_RESPONSE_JSON)
+
+    # Create Content object
+    content = genai_types.Content(
+        role="user", parts=[genai_types.Part(text="Hello from Content object")]
+    )
+
+    with mock.patch.object(
+        mock_genai_client._api_client, "request", return_value=mock_http_response
+    ):
+        with start_transaction(name="google_genai"):
+            mock_genai_client.models.generate_content(
+                model="gemini-1.5-flash", contents=content, config=create_test_config()
+            )
+
+    (event,) = events
+    invoke_span = event["spans"][0]
+
+    messages = json.loads(invoke_span["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES])
+    assert len(messages) == 1
+    assert messages[0]["role"] == "user"
+    assert messages[0]["content"] == [
+        {"text": "Hello from Content object", "type": "text"}
+    ]
+
+
+def test_generate_content_with_dict_format(
+    sentry_init, capture_events, mock_genai_client
+):
+    """Test generate_content with dict format input (ContentDict)."""
+    sentry_init(
+        integrations=[GoogleGenAIIntegration(include_prompts=True)],
+        traces_sample_rate=1.0,
+        send_default_pii=True,
+    )
+    events = capture_events()
+
+    mock_http_response = create_mock_http_response(EXAMPLE_API_RESPONSE_JSON)
+
+    # Dict format content
+    contents = {"role": "user", "parts": [{"text": "Hello from dict format"}]}
+
+    with mock.patch.object(
+        mock_genai_client._api_client, "request", return_value=mock_http_response
+    ):
+        with start_transaction(name="google_genai"):
+            mock_genai_client.models.generate_content(
+                model="gemini-1.5-flash", contents=contents, config=create_test_config()
+            )
+
+    (event,) = events
+    invoke_span = event["spans"][0]
+
+    messages = json.loads(invoke_span["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES])
+    assert len(messages) == 1
+    assert messages[0]["role"] == "user"
+    assert messages[0]["content"] == [
+        {"text": "Hello from dict format", "type": "text"}
+    ]
+
+
+def test_generate_content_with_file_data(
+    sentry_init, capture_events, mock_genai_client
+):
+    """Test generate_content with file_data (external file reference)."""
+    sentry_init(
+        integrations=[GoogleGenAIIntegration(include_prompts=True)],
+        traces_sample_rate=1.0,
+        send_default_pii=True,
+    )
+    events = capture_events()
+
+    mock_http_response = create_mock_http_response(EXAMPLE_API_RESPONSE_JSON)
+
+    # Content with file_data
+    file_data = genai_types.FileData(
+        file_uri="gs://bucket/image.jpg", mime_type="image/jpeg"
+    )
+    content = genai_types.Content(
+        role="user",
+        parts=[
+            genai_types.Part(text="What's in this image?"),
+            genai_types.Part(file_data=file_data),
+        ],
+    )
+
+    with mock.patch.object(
+        mock_genai_client._api_client, "request", return_value=mock_http_response
+    ):
+        with start_transaction(name="google_genai"):
+            mock_genai_client.models.generate_content(
+                model="gemini-1.5-flash", contents=content, config=create_test_config()
+            )
+
+    (event,) = events
+    invoke_span = event["spans"][0]
+
+    messages = json.loads(invoke_span["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES])
+    assert len(messages) == 1
+    assert messages[0]["role"] == "user"
+    assert len(messages[0]["content"]) == 2
+    assert messages[0]["content"][0] == {
+        "text": "What's in this image?",
+        "type": "text",
+    }
+    assert messages[0]["content"][1]["type"] == "uri"
+    assert messages[0]["content"][1]["modality"] == "image"
+    assert messages[0]["content"][1]["mime_type"] == "image/jpeg"
+    assert messages[0]["content"][1]["uri"] == "gs://bucket/image.jpg"
+
+
+def test_generate_content_with_inline_data(
+    sentry_init, capture_events, mock_genai_client
+):
+    """Test generate_content with inline_data (binary data)."""
+    sentry_init(
+        integrations=[GoogleGenAIIntegration(include_prompts=True)],
+        traces_sample_rate=1.0,
+        send_default_pii=True,
+    )
+    events = capture_events()
+
+    mock_http_response = create_mock_http_response(EXAMPLE_API_RESPONSE_JSON)
+
+    # Content with inline binary data
+    image_bytes = b"fake_image_binary_data"
+    blob = genai_types.Blob(data=image_bytes, mime_type="image/png")
+    content = genai_types.Content(
+        role="user",
+        parts=[
+            genai_types.Part(text="Describe this image"),
+            genai_types.Part(inline_data=blob),
+        ],
+    )
+
+    with mock.patch.object(
+        mock_genai_client._api_client, "request", return_value=mock_http_response
+    ):
+        with start_transaction(name="google_genai"):
+            mock_genai_client.models.generate_content(
+                model="gemini-1.5-flash", contents=content, config=create_test_config()
+            )
+
+    (event,) = events
+    invoke_span = event["spans"][0]
+
+    messages = json.loads(invoke_span["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES])
+    assert len(messages) == 1
+    assert messages[0]["role"] == "user"
+    assert len(messages[0]["content"]) == 2
+    assert messages[0]["content"][0] == {"text": "Describe this image", "type": "text"}
+    assert messages[0]["content"][1]["type"] == "blob"
+    assert messages[0]["content"][1]["mime_type"] == "image/png"
+    # Binary data should be substituted for privacy
+    assert messages[0]["content"][1]["content"] == BLOB_DATA_SUBSTITUTE
+
+
+def test_generate_content_with_function_response(
+    sentry_init, capture_events, mock_genai_client
+):
+    """Test generate_content with function_response (tool result)."""
+    sentry_init(
+        integrations=[GoogleGenAIIntegration(include_prompts=True)],
+        traces_sample_rate=1.0,
+        send_default_pii=True,
+    )
+    events = capture_events()
+
+    mock_http_response = create_mock_http_response(EXAMPLE_API_RESPONSE_JSON)
+
+    # Conversation with function response (tool result)
+    function_response = genai_types.FunctionResponse(
+        id="call_123", name="get_weather", response={"output": "Sunny, 72F"}
+    )
+    contents = [
+        genai_types.Content(
+            role="user", parts=[genai_types.Part(text="What's the weather in Paris?")]
+        ),
+        genai_types.Content(
+            role="user", parts=[genai_types.Part(function_response=function_response)]
+        ),
+    ]
+
+    with mock.patch.object(
+        mock_genai_client._api_client, "request", return_value=mock_http_response
+    ):
+        with start_transaction(name="google_genai"):
+            mock_genai_client.models.generate_content(
+                model="gemini-1.5-flash", contents=contents, config=create_test_config()
+            )
+
+    (event,) = events
+    invoke_span = event["spans"][0]
+
+    messages = json.loads(invoke_span["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES])
+    assert len(messages) == 1
+    # First message is user message
+    assert messages[0]["role"] == "tool"
+    assert messages[0]["content"]["toolCallId"] == "call_123"
+    assert messages[0]["content"]["toolName"] == "get_weather"
+    assert messages[0]["content"]["output"] == '"Sunny, 72F"'
+
+
+def test_generate_content_with_mixed_string_and_content(
+    sentry_init, capture_events, mock_genai_client
+):
+    """Test generate_content with mixed string and Content objects in list."""
+    sentry_init(
+        integrations=[GoogleGenAIIntegration(include_prompts=True)],
+        traces_sample_rate=1.0,
+        send_default_pii=True,
+    )
+    events = capture_events()
+
+    mock_http_response = create_mock_http_response(EXAMPLE_API_RESPONSE_JSON)
+
+    # Mix of strings and Content objects
+    contents = [
+        "Hello, this is a string message",
+        genai_types.Content(
+            role="model",
+            parts=[genai_types.Part(text="Hi! How can I help you?")],
+        ),
+        genai_types.Content(
+            role="user",
+            parts=[genai_types.Part(text="Tell me a joke")],
+        ),
+    ]
+
+    with mock.patch.object(
+        mock_genai_client._api_client, "request", return_value=mock_http_response
+    ):
+        with start_transaction(name="google_genai"):
+            mock_genai_client.models.generate_content(
+                model="gemini-1.5-flash", contents=contents, config=create_test_config()
+            )
+
+    (event,) = events
+    invoke_span = event["spans"][0]
+
+    messages = json.loads(invoke_span["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES])
+    assert len(messages) == 1
+    # User message
+    assert messages[0]["role"] == "user"
+    assert messages[0]["content"] == [{"text": "Tell me a joke", "type": "text"}]
+
+
+def test_generate_content_with_part_object_directly(
+    sentry_init, capture_events, mock_genai_client
+):
+    """Test generate_content with Part object directly (not wrapped in Content)."""
+    sentry_init(
+        integrations=[GoogleGenAIIntegration(include_prompts=True)],
+        traces_sample_rate=1.0,
+        send_default_pii=True,
+    )
+    events = capture_events()
+
+    mock_http_response = create_mock_http_response(EXAMPLE_API_RESPONSE_JSON)
+
+    # Part object directly
+    part = genai_types.Part(text="Direct Part object")
+
+    with mock.patch.object(
+        mock_genai_client._api_client, "request", return_value=mock_http_response
+    ):
+        with start_transaction(name="google_genai"):
+            mock_genai_client.models.generate_content(
+                model="gemini-1.5-flash", contents=part, config=create_test_config()
+            )
+
+    (event,) = events
+    invoke_span = event["spans"][0]
+
+    messages = json.loads(invoke_span["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES])
+    assert len(messages) == 1
+    assert messages[0]["role"] == "user"
+    assert messages[0]["content"] == [{"text": "Direct Part object", "type": "text"}]
+
+
+def test_generate_content_with_list_of_dicts(
+    sentry_init, capture_events, mock_genai_client
+):
+    """Test generate_content with list of dict format inputs."""
+    sentry_init(
+        integrations=[GoogleGenAIIntegration(include_prompts=True)],
+        traces_sample_rate=1.0,
+        send_default_pii=True,
+    )
+    events = capture_events()
+
+    mock_http_response = create_mock_http_response(EXAMPLE_API_RESPONSE_JSON)
+
+    # List of dicts (conversation in dict format)
+    contents = [
+        {"role": "user", "parts": [{"text": "First user message"}]},
+        {"role": "model", "parts": [{"text": "First model response"}]},
+        {"role": "user", "parts": [{"text": "Second user message"}]},
+    ]
+
+    with mock.patch.object(
+        mock_genai_client._api_client, "request", return_value=mock_http_response
+    ):
+        with start_transaction(name="google_genai"):
+            mock_genai_client.models.generate_content(
+                model="gemini-1.5-flash", contents=contents, config=create_test_config()
+            )
+
+    (event,) = events
+    invoke_span = event["spans"][0]
+
+    messages = json.loads(invoke_span["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES])
+    assert len(messages) == 1
+    assert messages[0]["role"] == "user"
+    assert messages[0]["content"] == [{"text": "Second user message", "type": "text"}]
+
+
+def test_generate_content_with_dict_inline_data(
+    sentry_init, capture_events, mock_genai_client
+):
+    """Test generate_content with dict format containing inline_data."""
+    sentry_init(
+        integrations=[GoogleGenAIIntegration(include_prompts=True)],
+        traces_sample_rate=1.0,
+        send_default_pii=True,
+    )
+    events = capture_events()
+
+    mock_http_response = create_mock_http_response(EXAMPLE_API_RESPONSE_JSON)
+
+    # Dict with inline_data
+    contents = {
+        "role": "user",
+        "parts": [
+            {"text": "What's in this image?"},
+            {"inline_data": {"data": b"fake_binary_data", "mime_type": "image/gif"}},
+        ],
+    }
+
+    with mock.patch.object(
+        mock_genai_client._api_client, "request", return_value=mock_http_response
+    ):
+        with start_transaction(name="google_genai"):
+            mock_genai_client.models.generate_content(
+                model="gemini-1.5-flash", contents=contents, config=create_test_config()
+            )
+
+    (event,) = events
+    invoke_span = event["spans"][0]
+
+    messages = json.loads(invoke_span["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES])
+    assert len(messages) == 1
+    assert messages[0]["role"] == "user"
+    assert len(messages[0]["content"]) == 2
+    assert messages[0]["content"][0] == {
+        "text": "What's in this image?",
+        "type": "text",
+    }
+    assert messages[0]["content"][1]["type"] == "blob"
+    assert messages[0]["content"][1]["mime_type"] == "image/gif"
+    assert messages[0]["content"][1]["content"] == BLOB_DATA_SUBSTITUTE
+
+
+# Tests for extract_contents_messages function
+def test_extract_contents_messages_none():
+    """Test extract_contents_messages with None input"""
+    result = extract_contents_messages(None)
+    assert result == []
+
+
+def test_extract_contents_messages_string():
+    """Test extract_contents_messages with string input"""
+    result = extract_contents_messages("Hello world")
+    assert result == [{"role": "user", "content": "Hello world"}]
+
+
+def test_extract_contents_messages_content_object():
+    """Test extract_contents_messages with Content object"""
+    content = genai_types.Content(
+        role="user", parts=[genai_types.Part(text="Test message")]
+    )
+    result = extract_contents_messages(content)
+    assert len(result) == 1
+    assert result[0]["role"] == "user"
+    assert result[0]["content"] == [{"text": "Test message", "type": "text"}]
+
+
+def test_extract_contents_messages_content_object_model_role():
+    """Test extract_contents_messages with Content object having model role"""
+    content = genai_types.Content(
+        role="model", parts=[genai_types.Part(text="Assistant response")]
+    )
+    result = extract_contents_messages(content)
+    assert len(result) == 1
+    assert result[0]["role"] == "assistant"
+    assert result[0]["content"] == [{"text": "Assistant response", "type": "text"}]
+
+
+def test_extract_contents_messages_content_object_no_role():
+    """Test extract_contents_messages with Content object without role"""
+    content = genai_types.Content(parts=[genai_types.Part(text="No role message")])
+    result = extract_contents_messages(content)
+    assert len(result) == 1
+    assert result[0]["role"] == "user"
+    assert result[0]["content"] == [{"text": "No role message", "type": "text"}]
+
+
+def test_extract_contents_messages_part_object():
+    """Test extract_contents_messages with Part object"""
+    part = genai_types.Part(text="Direct part")
+    result = extract_contents_messages(part)
+    assert len(result) == 1
+    assert result[0]["role"] == "user"
+    assert result[0]["content"] == [{"text": "Direct part", "type": "text"}]
+
+
+def test_extract_contents_messages_file_data():
+    """Test extract_contents_messages with file_data"""
+    file_data = genai_types.FileData(
+        file_uri="gs://bucket/file.jpg", mime_type="image/jpeg"
+    )
+    part = genai_types.Part(file_data=file_data)
+    content = genai_types.Content(parts=[part])
+    result = extract_contents_messages(content)
+
+    assert len(result) == 1
+    assert result[0]["role"] == "user"
+    assert len(result[0]["content"]) == 1
+    blob_part = result[0]["content"][0]
+    assert blob_part["type"] == "uri"
+    assert blob_part["modality"] == "image"
+    assert blob_part["mime_type"] == "image/jpeg"
+    assert blob_part["uri"] == "gs://bucket/file.jpg"
+
+
+def test_extract_contents_messages_inline_data():
+    """Test extract_contents_messages with inline_data (binary)"""
+    # Create inline data with bytes
+    image_bytes = b"fake_image_data"
+    blob = genai_types.Blob(data=image_bytes, mime_type="image/png")
+    part = genai_types.Part(inline_data=blob)
+    content = genai_types.Content(parts=[part])
+    result = extract_contents_messages(content)
+
+    assert len(result) == 1
+    assert result[0]["role"] == "user"
+    assert len(result[0]["content"]) == 1
+    blob_part = result[0]["content"][0]
+    assert blob_part["type"] == "blob"
+    assert blob_part["mime_type"] == "image/png"
+    assert blob_part["content"] == BLOB_DATA_SUBSTITUTE
+
+
+def test_extract_contents_messages_function_response():
+    """Test extract_contents_messages with function_response (tool message)"""
+    function_response = genai_types.FunctionResponse(
+        id="call_123", name="get_weather", response={"output": "sunny"}
+    )
+    part = genai_types.Part(function_response=function_response)
+    content = genai_types.Content(parts=[part])
+    result = extract_contents_messages(content)
+
+    assert len(result) == 1
+    assert result[0]["role"] == "tool"
+    assert result[0]["content"]["toolCallId"] == "call_123"
+    assert result[0]["content"]["toolName"] == "get_weather"
+    assert result[0]["content"]["output"] == '"sunny"'
+
+
+def test_extract_contents_messages_function_response_with_output_key():
+    """Test extract_contents_messages with function_response that has output key"""
+    function_response = genai_types.FunctionResponse(
+        id="call_456", name="get_time", response={"output": "3:00 PM", "error": None}
+    )
+    part = genai_types.Part(function_response=function_response)
+    content = genai_types.Content(parts=[part])
+    result = extract_contents_messages(content)
+
+    assert len(result) == 1
+    assert result[0]["role"] == "tool"
+    assert result[0]["content"]["toolCallId"] == "call_456"
+    assert result[0]["content"]["toolName"] == "get_time"
+    # Should prefer "output" key
+    assert result[0]["content"]["output"] == '"3:00 PM"'
+
+
+def test_extract_contents_messages_mixed_parts():
+    """Test extract_contents_messages with mixed content parts"""
+    content = genai_types.Content(
+        role="user",
+        parts=[
+            genai_types.Part(text="Text part"),
+            genai_types.Part(
+                file_data=genai_types.FileData(
+                    file_uri="gs://bucket/image.jpg", mime_type="image/jpeg"
+                )
+            ),
+        ],
+    )
+    result = extract_contents_messages(content)
+
+    assert len(result) == 1
+    assert result[0]["role"] == "user"
+    assert len(result[0]["content"]) == 2
+    assert result[0]["content"][0] == {"text": "Text part", "type": "text"}
+    assert result[0]["content"][1]["type"] == "uri"
+    assert result[0]["content"][1]["modality"] == "image"
+    assert result[0]["content"][1]["uri"] == "gs://bucket/image.jpg"
+
+
+def test_extract_contents_messages_list():
+    """Test extract_contents_messages with list input"""
+    contents = [
+        "First message",
+        genai_types.Content(
+            role="user", parts=[genai_types.Part(text="Second message")]
+        ),
+    ]
+    result = extract_contents_messages(contents)
+
+    assert len(result) == 2
+    assert result[0] == {"role": "user", "content": "First message"}
+    assert result[1]["role"] == "user"
+    assert result[1]["content"] == [{"text": "Second message", "type": "text"}]
+
+
+def test_extract_contents_messages_dict_content():
+    """Test extract_contents_messages with dict (ContentDict)"""
+    content_dict = {"role": "user", "parts": [{"text": "Dict message"}]}
+    result = extract_contents_messages(content_dict)
+
+    assert len(result) == 1
+    assert result[0]["role"] == "user"
+    assert result[0]["content"] == [{"text": "Dict message", "type": "text"}]
+
+
+def test_extract_contents_messages_dict_with_text():
+    """Test extract_contents_messages with dict containing text key"""
+    content_dict = {"role": "user", "text": "Simple text"}
+    result = extract_contents_messages(content_dict)
+
+    assert len(result) == 1
+    assert result[0]["role"] == "user"
+    assert result[0]["content"] == [{"text": "Simple text", "type": "text"}]
+
+
+def test_extract_contents_messages_file_object():
+    """Test extract_contents_messages with File object"""
+    file_obj = genai_types.File(
+        name="files/123", uri="gs://bucket/file.pdf", mime_type="application/pdf"
+    )
+    result = extract_contents_messages(file_obj)
+
+    assert len(result) == 1
+    assert result[0]["role"] == "user"
+    assert len(result[0]["content"]) == 1
+    blob_part = result[0]["content"][0]
+    assert blob_part["type"] == "uri"
+    assert blob_part["modality"] == "document"
+    assert blob_part["mime_type"] == "application/pdf"
+    assert blob_part["uri"] == "gs://bucket/file.pdf"
+
+
+@pytest.mark.skipif(
+    not hasattr(genai_types, "PIL_Image") or genai_types.PIL_Image is None,
+    reason="PIL not available",
+)
+def test_extract_contents_messages_pil_image():
+    """Test extract_contents_messages with PIL.Image.Image"""
+    try:
+        from PIL import Image as PILImage
+
+        # Create a simple test image
+        img = PILImage.new("RGB", (10, 10), color="red")
+        result = extract_contents_messages(img)
+
+        assert len(result) == 1
+        assert result[0]["role"] == "user"
+        assert len(result[0]["content"]) == 1
+        blob_part = result[0]["content"][0]
+        assert blob_part["type"] == "blob"
+        assert blob_part["mime_type"].startswith("image/")
+        assert "content" in blob_part
+        # Binary content is substituted with placeholder for privacy
+        assert blob_part["content"] == "[Blob substitute]"
+    except ImportError:
+        pytest.skip("PIL not available")
+
+
+def test_extract_contents_messages_tool_and_text():
+    """Test extract_contents_messages with both tool message and text"""
+    content = genai_types.Content(
+        role="user",
+        parts=[
+            genai_types.Part(text="User question"),
+            genai_types.Part(
+                function_response=genai_types.FunctionResponse(
+                    id="call_789", name="search", response={"output": "results"}
+                )
+            ),
+        ],
+    )
+    result = extract_contents_messages(content)
+
+    # Should have two messages: one user message and one tool message
+    assert len(result) == 2
+    # First should be user message with text
+    assert result[0]["role"] == "user"
+    assert result[0]["content"] == [{"text": "User question", "type": "text"}]
+    # Second should be tool message
+    assert result[1]["role"] == "tool"
+    assert result[1]["content"]["toolCallId"] == "call_789"
+    assert result[1]["content"]["toolName"] == "search"
+
+
+def test_extract_contents_messages_empty_parts():
+    """Test extract_contents_messages with Content object with empty parts"""
+    content = genai_types.Content(role="user", parts=[])
+    result = extract_contents_messages(content)
+
+    assert result == []
+
+
+def test_extract_contents_messages_empty_list():
+    """Test extract_contents_messages with empty list"""
+    result = extract_contents_messages([])
+    assert result == []
+
+
+def test_extract_contents_messages_dict_inline_data():
+    """Test extract_contents_messages with dict containing inline_data"""
+    content_dict = {
+        "role": "user",
+        "parts": [{"inline_data": {"data": b"binary_data", "mime_type": "image/gif"}}],
+    }
+    result = extract_contents_messages(content_dict)
+
+    assert len(result) == 1
+    assert result[0]["role"] == "user"
+    assert len(result[0]["content"]) == 1
+    blob_part = result[0]["content"][0]
+    assert blob_part["type"] == "blob"
+    assert blob_part["mime_type"] == "image/gif"
+    assert blob_part["content"] == BLOB_DATA_SUBSTITUTE
+
+
+def test_extract_contents_messages_dict_function_response():
+    """Test extract_contents_messages with dict containing function_response"""
+    content_dict = {
+        "role": "user",
+        "parts": [
+            {
+                "function_response": {
+                    "id": "dict_call_1",
+                    "name": "dict_tool",
+                    "response": {"result": "success"},
+                }
+            }
+        ],
+    }
+    result = extract_contents_messages(content_dict)
+
+    assert len(result) == 1
+    assert result[0]["role"] == "tool"
+    assert result[0]["content"]["toolCallId"] == "dict_call_1"
+    assert result[0]["content"]["toolName"] == "dict_tool"
+    assert result[0]["content"]["output"] == '{"result": "success"}'
+
+
+def test_extract_contents_messages_object_with_text_attribute():
+    """Test extract_contents_messages with object that has text attribute"""
+
+    class TextObject:
+        def __init__(self):
+            self.text = "Object text"
+
+    obj = TextObject()
+    result = extract_contents_messages(obj)
+
+    assert len(result) == 1
+    assert result[0]["role"] == "user"
+    assert result[0]["content"] == [{"text": "Object text", "type": "text"}]
diff --git a/tests/integrations/gql/test_gql.py b/tests/integrations/gql/test_gql.py
index 147f7a06a8..2785c63e2c 100644
--- a/tests/integrations/gql/test_gql.py
+++ b/tests/integrations/gql/test_gql.py
@@ -3,9 +3,13 @@
 import responses
 from gql import gql
 from gql import Client
+from gql import __version__
 from gql.transport.exceptions import TransportQueryError
 from gql.transport.requests import RequestsHTTPTransport
 from sentry_sdk.integrations.gql import GQLIntegration
+from sentry_sdk.utils import parse_version
+
+GQL_VERSION = parse_version(__version__)
 
 
 @responses.activate
@@ -32,7 +36,36 @@ def _execute_mock_query(response_json):
     return client.execute(query)
 
 
-def _make_erroneous_query(capture_events):
+@responses.activate
+def _execute_mock_query_with_keyword_document(response_json):
+    url = "http://example.com/graphql"
+    query_string = """
+        query Example {
+            example
+        }
+    """
+
+    # Mock the GraphQL server response
+    responses.add(
+        method=responses.POST,
+        url=url,
+        json=response_json,
+        status=200,
+    )
+
+    transport = RequestsHTTPTransport(url=url)
+    client = Client(transport=transport)
+    query = gql(query_string)
+
+    return client.execute(document=query)
+
+
+_execute_query_funcs = [_execute_mock_query]
+if GQL_VERSION < (4,):
+    _execute_query_funcs.append(_execute_mock_query_with_keyword_document)
+
+
+def _make_erroneous_query(capture_events, execute_query):
     """
     Make an erroneous GraphQL query, and assert that the error was reraised, that
     exactly one event was recorded, and that the exception recorded was a
@@ -42,7 +75,7 @@ def _make_erroneous_query(capture_events):
     response_json = {"errors": ["something bad happened"]}
 
     with pytest.raises(TransportQueryError):
-        _execute_mock_query(response_json)
+        execute_query(response_json)
 
     assert len(events) == 1, (
         "the sdk captured %d events, but 1 event was expected" % len(events)
@@ -67,7 +100,8 @@ def test_gql_init(sentry_init):
     sentry_init(integrations=[GQLIntegration()])
 
 
-def test_real_gql_request_no_error(sentry_init, capture_events):
+@pytest.mark.parametrize("execute_query", _execute_query_funcs)
+def test_real_gql_request_no_error(sentry_init, capture_events, execute_query):
     """
     Integration test verifying that the GQLIntegration works as expected with successful query.
     """
@@ -77,7 +111,7 @@ def test_real_gql_request_no_error(sentry_init, capture_events):
     response_data = {"example": "This is the example"}
     response_json = {"data": response_data}
 
-    result = _execute_mock_query(response_json)
+    result = execute_query(response_json)
 
     assert result == response_data, (
         "client.execute returned a different value from what it received from the server"
@@ -87,27 +121,31 @@ def test_real_gql_request_no_error(sentry_init, capture_events):
     )
 
 
-def test_real_gql_request_with_error_no_pii(sentry_init, capture_events):
+@pytest.mark.parametrize("execute_query", _execute_query_funcs)
+def test_real_gql_request_with_error_no_pii(sentry_init, capture_events, execute_query):
     """
     Integration test verifying that the GQLIntegration works as expected with query resulting
     in a GraphQL error, and that PII is not sent.
     """
     sentry_init(integrations=[GQLIntegration()])
 
-    event = _make_erroneous_query(capture_events)
+    event = _make_erroneous_query(capture_events, execute_query)
 
     assert "data" not in event["request"]
     assert "response" not in event["contexts"]
 
 
-def test_real_gql_request_with_error_with_pii(sentry_init, capture_events):
+@pytest.mark.parametrize("execute_query", _execute_query_funcs)
+def test_real_gql_request_with_error_with_pii(
+    sentry_init, capture_events, execute_query
+):
     """
     Integration test verifying that the GQLIntegration works as expected with query resulting
     in a GraphQL error, and that PII is not sent.
     """
     sentry_init(integrations=[GQLIntegration()], send_default_pii=True)
 
-    event = _make_erroneous_query(capture_events)
+    event = _make_erroneous_query(capture_events, execute_query)
 
     assert "data" in event["request"]
     assert "response" in event["contexts"]
diff --git a/tests/integrations/grpc/test_grpc.py b/tests/integrations/grpc/test_grpc.py
index 8d2698f411..25436d9feb 100644
--- a/tests/integrations/grpc/test_grpc.py
+++ b/tests/integrations/grpc/test_grpc.py
@@ -8,6 +8,7 @@
 from sentry_sdk import start_span, start_transaction
 from sentry_sdk.consts import OP
 from sentry_sdk.integrations.grpc import GRPCIntegration
+from sentry_sdk.integrations.grpc.client import ClientInterceptor
 from tests.conftest import ApproxDict
 from tests.integrations.grpc.grpc_test_service_pb2 import gRPCTestMessage
 from tests.integrations.grpc.grpc_test_service_pb2_grpc import (
@@ -269,6 +270,42 @@ def test_grpc_client_other_interceptor(sentry_init, capture_events_forksafe):
     )
 
 
+@pytest.mark.forked
+def test_prevent_dual_client_interceptor(sentry_init, capture_events_forksafe):
+    sentry_init(traces_sample_rate=1.0, integrations=[GRPCIntegration()])
+    events = capture_events_forksafe()
+
+    server, channel = _set_up()
+
+    # Intercept the channel
+    channel = grpc.intercept_channel(channel, ClientInterceptor())
+    stub = gRPCTestServiceStub(channel)
+
+    with start_transaction():
+        stub.TestServe(gRPCTestMessage(text="test"))
+
+    _tear_down(server=server)
+
+    events.write_file.close()
+    events.read_event()
+    local_transaction = events.read_event()
+    span = local_transaction["spans"][0]
+
+    assert len(local_transaction["spans"]) == 1
+    assert span["op"] == OP.GRPC_CLIENT
+    assert (
+        span["description"]
+        == "unary unary call to /grpc_test_server.gRPCTestService/TestServe"
+    )
+    assert span["data"] == ApproxDict(
+        {
+            "type": "unary unary",
+            "method": "/grpc_test_server.gRPCTestService/TestServe",
+            "code": "OK",
+        }
+    )
+
+
 @pytest.mark.forked
 def test_grpc_client_and_servers_interceptors_integration(
     sentry_init, capture_events_forksafe
diff --git a/tests/integrations/langchain/test_langchain.py b/tests/integrations/langchain/test_langchain.py
index 114e819bfb..58cc16cdd7 100644
--- a/tests/integrations/langchain/test_langchain.py
+++ b/tests/integrations/langchain/test_langchain.py
@@ -25,6 +25,8 @@
 from sentry_sdk.integrations.langchain import (
     LangchainIntegration,
     SentryLangchainCallback,
+    _transform_langchain_content_block,
+    _transform_langchain_message_content,
 )
 
 try:
@@ -73,8 +75,26 @@ def _llm_type(self) -> str:
         (False, False, True),
     ],
 )
+@pytest.mark.parametrize(
+    "system_instructions_content",
+    [
+        "You are very powerful assistant, but don't know current events",
+        ["You are a helpful assistant.", "Be concise and clear."],
+        [
+            {"type": "text", "text": "You are a helpful assistant."},
+            {"type": "text", "text": "Be concise and clear."},
+        ],
+    ],
+    ids=["string", "list", "blocks"],
+)
 def test_langchain_agent(
-    sentry_init, capture_events, send_default_pii, include_prompts, use_unknown_llm_type
+    sentry_init,
+    capture_events,
+    send_default_pii,
+    include_prompts,
+    use_unknown_llm_type,
+    system_instructions_content,
+    request,
 ):
     global llm_type
     llm_type = "acme-llm" if use_unknown_llm_type else "openai-chat"
@@ -94,7 +114,7 @@ def test_langchain_agent(
         [
             (
                 "system",
-                "You are very powerful assistant, but don't know current events",
+                system_instructions_content,
             ),
             ("user", "{input}"),
             MessagesPlaceholder(variable_name="agent_scratchpad"),
@@ -215,17 +235,30 @@ def test_langchain_agent(
         assert chat_spans[1]["data"]["gen_ai.usage.total_tokens"] == 117
 
     if send_default_pii and include_prompts:
-        assert (
-            "You are very powerful"
-            in chat_spans[0]["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES]
-        )
         assert "5" in chat_spans[0]["data"][SPANDATA.GEN_AI_RESPONSE_TEXT]
         assert "word" in tool_exec_span["data"][SPANDATA.GEN_AI_TOOL_INPUT]
         assert 5 == int(tool_exec_span["data"][SPANDATA.GEN_AI_TOOL_OUTPUT])
-        assert (
-            "You are very powerful"
-            in chat_spans[1]["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES]
-        )
+
+        param_id = request.node.callspec.id
+        if "string" in param_id:
+            assert [
+                {
+                    "type": "text",
+                    "content": "You are very powerful assistant, but don't know current events",
+                }
+            ] == json.loads(chat_spans[0]["data"][SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS])
+        else:
+            assert [
+                {
+                    "type": "text",
+                    "content": "You are a helpful assistant.",
+                },
+                {
+                    "type": "text",
+                    "content": "Be concise and clear.",
+                },
+            ] == json.loads(chat_spans[0]["data"][SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS])
+
         assert "5" in chat_spans[1]["data"][SPANDATA.GEN_AI_RESPONSE_TEXT]
 
         # Verify tool calls are recorded when PII is enabled
@@ -241,8 +274,10 @@ def test_langchain_agent(
             tool_call_str = str(tool_calls_data)
             assert "get_word_length" in tool_call_str
     else:
+        assert SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS not in chat_spans[0].get("data", {})
         assert SPANDATA.GEN_AI_REQUEST_MESSAGES not in chat_spans[0].get("data", {})
         assert SPANDATA.GEN_AI_RESPONSE_TEXT not in chat_spans[0].get("data", {})
+        assert SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS not in chat_spans[1].get("data", {})
         assert SPANDATA.GEN_AI_REQUEST_MESSAGES not in chat_spans[1].get("data", {})
         assert SPANDATA.GEN_AI_RESPONSE_TEXT not in chat_spans[1].get("data", {})
         assert SPANDATA.GEN_AI_TOOL_INPUT not in tool_exec_span.get("data", {})
@@ -1033,9 +1068,10 @@ def test_langchain_message_truncation(sentry_init, capture_events):
 
     parsed_messages = json.loads(messages_data)
     assert isinstance(parsed_messages, list)
-    assert len(parsed_messages) == 2
-    assert "small message 4" in str(parsed_messages[0])
-    assert "small message 5" in str(parsed_messages[1])
+    assert len(parsed_messages) == 1
+    assert "small message 5" in str(parsed_messages[0])
+
+    assert llm_span["data"][SPANDATA.META_GEN_AI_ORIGINAL_INPUT_MESSAGES_LENGTH] == 5
     assert tx["_meta"]["spans"]["0"]["data"]["gen_ai.request.messages"][""]["len"] == 5
 
 
@@ -1747,3 +1783,330 @@ def test_langchain_response_model_extraction(
         assert llm_span["data"][SPANDATA.GEN_AI_RESPONSE_MODEL] == expected_model
     else:
         assert SPANDATA.GEN_AI_RESPONSE_MODEL not in llm_span.get("data", {})
+
+
+# Tests for multimodal content transformation functions
+
+
+class TestTransformLangchainContentBlock:
+    """Tests for _transform_langchain_content_block function."""
+
+    def test_transform_image_base64(self):
+        """Test transformation of base64-encoded image content."""
+        content_block = {
+            "type": "image",
+            "base64": "/9j/4AAQSkZJRgABAQAAAQABAAD...",
+            "mime_type": "image/jpeg",
+        }
+        result = _transform_langchain_content_block(content_block)
+        assert result == {
+            "type": "blob",
+            "modality": "image",
+            "mime_type": "image/jpeg",
+            "content": "/9j/4AAQSkZJRgABAQAAAQABAAD...",
+        }
+
+    def test_transform_image_url(self):
+        """Test transformation of URL-referenced image content."""
+        content_block = {
+            "type": "image",
+            "url": "https://example.com/image.jpg",
+            "mime_type": "image/jpeg",
+        }
+        result = _transform_langchain_content_block(content_block)
+        assert result == {
+            "type": "uri",
+            "modality": "image",
+            "mime_type": "image/jpeg",
+            "uri": "https://example.com/image.jpg",
+        }
+
+    def test_transform_image_file_id(self):
+        """Test transformation of file_id-referenced image content."""
+        content_block = {
+            "type": "image",
+            "file_id": "file-abc123",
+            "mime_type": "image/png",
+        }
+        result = _transform_langchain_content_block(content_block)
+        assert result == {
+            "type": "file",
+            "modality": "image",
+            "mime_type": "image/png",
+            "file_id": "file-abc123",
+        }
+
+    def test_transform_image_url_legacy_with_data_uri(self):
+        """Test transformation of legacy image_url format with data: URI (base64)."""
+        content_block = {
+            "type": "image_url",
+            "image_url": {"url": "data:image/jpeg;base64,/9j/4AAQSkZJRgABAQAAAQABAAD"},
+        }
+        result = _transform_langchain_content_block(content_block)
+        assert result == {
+            "type": "blob",
+            "modality": "image",
+            "mime_type": "image/jpeg",
+            "content": "/9j/4AAQSkZJRgABAQAAAQABAAD",
+        }
+
+    def test_transform_image_url_legacy_with_http_url(self):
+        """Test transformation of legacy image_url format with HTTP URL."""
+        content_block = {
+            "type": "image_url",
+            "image_url": {"url": "https://example.com/image.png"},
+        }
+        result = _transform_langchain_content_block(content_block)
+        assert result == {
+            "type": "uri",
+            "modality": "image",
+            "mime_type": "",
+            "uri": "https://example.com/image.png",
+        }
+
+    def test_transform_image_url_legacy_string_url(self):
+        """Test transformation of legacy image_url format with string URL."""
+        content_block = {
+            "type": "image_url",
+            "image_url": "https://example.com/image.gif",
+        }
+        result = _transform_langchain_content_block(content_block)
+        assert result == {
+            "type": "uri",
+            "modality": "image",
+            "mime_type": "",
+            "uri": "https://example.com/image.gif",
+        }
+
+    def test_transform_image_url_legacy_data_uri_png(self):
+        """Test transformation of legacy image_url format with PNG data URI."""
+        content_block = {
+            "type": "image_url",
+            "image_url": {
+                "url": "data:image/png;base64,iVBORw0KGgoAAAANSUhEUgAAAAEAAAABCAYAAAAfFcSJAAAADUlEQVR42mNk+M9QDwADhgGAWjR9awAAAABJRU5ErkJggg=="
+            },
+        }
+        result = _transform_langchain_content_block(content_block)
+        assert result == {
+            "type": "blob",
+            "modality": "image",
+            "mime_type": "image/png",
+            "content": "iVBORw0KGgoAAAANSUhEUgAAAAEAAAABCAYAAAAfFcSJAAAADUlEQVR42mNk+M9QDwADhgGAWjR9awAAAABJRU5ErkJggg==",
+        }
+
+    def test_transform_missing_mime_type(self):
+        """Test transformation when mime_type is not provided."""
+        content_block = {
+            "type": "image",
+            "base64": "/9j/4AAQSkZJRgABAQAAAQABAAD...",
+        }
+        result = _transform_langchain_content_block(content_block)
+        assert result == {
+            "type": "blob",
+            "modality": "image",
+            "mime_type": "",
+            "content": "/9j/4AAQSkZJRgABAQAAAQABAAD...",
+        }
+
+    def test_transform_anthropic_source_base64(self):
+        """Test transformation of Anthropic-style image with base64 source."""
+        content_block = {
+            "type": "image",
+            "source": {
+                "type": "base64",
+                "media_type": "image/png",
+                "data": "iVBORw0KGgoAAAANSUhEUgAAAAE...",
+            },
+        }
+        result = _transform_langchain_content_block(content_block)
+        assert result == {
+            "type": "blob",
+            "modality": "image",
+            "mime_type": "image/png",
+            "content": "iVBORw0KGgoAAAANSUhEUgAAAAE...",
+        }
+
+    def test_transform_anthropic_source_url(self):
+        """Test transformation of Anthropic-style image with URL source."""
+        content_block = {
+            "type": "image",
+            "source": {
+                "type": "url",
+                "media_type": "image/jpeg",
+                "url": "https://example.com/image.jpg",
+            },
+        }
+        result = _transform_langchain_content_block(content_block)
+        assert result == {
+            "type": "uri",
+            "modality": "image",
+            "mime_type": "image/jpeg",
+            "uri": "https://example.com/image.jpg",
+        }
+
+    def test_transform_anthropic_source_without_media_type(self):
+        """Test transformation of Anthropic-style image without media_type uses empty mime_type."""
+        content_block = {
+            "type": "image",
+            "mime_type": "image/webp",  # Top-level mime_type is ignored by standard Anthropic format
+            "source": {
+                "type": "base64",
+                "data": "UklGRh4AAABXRUJQVlA4IBIAAAAwAQCdASoBAAEAAQAcJYgCdAEO",
+            },
+        }
+        result = _transform_langchain_content_block(content_block)
+        # Note: The shared transform_content_part uses media_type from source, not top-level mime_type
+        assert result == {
+            "type": "blob",
+            "modality": "image",
+            "mime_type": "",
+            "content": "UklGRh4AAABXRUJQVlA4IBIAAAAwAQCdASoBAAEAAQAcJYgCdAEO",
+        }
+
+    def test_transform_google_inline_data(self):
+        """Test transformation of Google-style inline_data format."""
+        content_block = {
+            "inline_data": {
+                "mime_type": "image/jpeg",
+                "data": "/9j/4AAQSkZJRgABAQAAAQABAAD...",
+            }
+        }
+        result = _transform_langchain_content_block(content_block)
+        assert result == {
+            "type": "blob",
+            "modality": "image",
+            "mime_type": "image/jpeg",
+            "content": "/9j/4AAQSkZJRgABAQAAAQABAAD...",
+        }
+
+    def test_transform_google_file_data(self):
+        """Test transformation of Google-style file_data format."""
+        content_block = {
+            "file_data": {
+                "mime_type": "image/png",
+                "file_uri": "gs://bucket/path/to/image.png",
+            }
+        }
+        result = _transform_langchain_content_block(content_block)
+        assert result == {
+            "type": "uri",
+            "modality": "image",
+            "mime_type": "image/png",
+            "uri": "gs://bucket/path/to/image.png",
+        }
+
+
+class TestTransformLangchainMessageContent:
+    """Tests for _transform_langchain_message_content function."""
+
+    def test_transform_string_content(self):
+        """Test that string content is returned unchanged."""
+        result = _transform_langchain_message_content("Hello, world!")
+        assert result == "Hello, world!"
+
+    def test_transform_list_with_text_blocks(self):
+        """Test transformation of list with text blocks (unchanged)."""
+        content = [
+            {"type": "text", "text": "First message"},
+            {"type": "text", "text": "Second message"},
+        ]
+        result = _transform_langchain_message_content(content)
+        assert result == content
+
+    def test_transform_list_with_image_blocks(self):
+        """Test transformation of list containing image blocks."""
+        content = [
+            {"type": "text", "text": "Check out this image:"},
+            {
+                "type": "image",
+                "base64": "/9j/4AAQSkZJRgABAQAAAQABAAD...",
+                "mime_type": "image/jpeg",
+            },
+        ]
+        result = _transform_langchain_message_content(content)
+        assert len(result) == 2
+        assert result[0] == {"type": "text", "text": "Check out this image:"}
+        assert result[1] == {
+            "type": "blob",
+            "modality": "image",
+            "mime_type": "image/jpeg",
+            "content": "/9j/4AAQSkZJRgABAQAAAQABAAD...",
+        }
+
+    def test_transform_list_with_mixed_content(self):
+        """Test transformation of list with mixed content types."""
+        content = [
+            {"type": "text", "text": "Here are some files:"},
+            {
+                "type": "image",
+                "url": "https://example.com/image.jpg",
+                "mime_type": "image/jpeg",
+            },
+            {
+                "type": "file",
+                "file_id": "doc-123",
+                "mime_type": "application/pdf",
+            },
+            {"type": "audio", "base64": "audio_data...", "mime_type": "audio/mp3"},
+        ]
+        result = _transform_langchain_message_content(content)
+        assert len(result) == 4
+        assert result[0] == {"type": "text", "text": "Here are some files:"}
+        assert result[1] == {
+            "type": "uri",
+            "modality": "image",
+            "mime_type": "image/jpeg",
+            "uri": "https://example.com/image.jpg",
+        }
+        assert result[2] == {
+            "type": "file",
+            "modality": "document",
+            "mime_type": "application/pdf",
+            "file_id": "doc-123",
+        }
+        assert result[3] == {
+            "type": "blob",
+            "modality": "audio",
+            "mime_type": "audio/mp3",
+            "content": "audio_data...",
+        }
+
+    def test_transform_list_with_non_dict_items(self):
+        """Test transformation handles non-dict items in list."""
+        content = ["plain string", {"type": "text", "text": "dict text"}]
+        result = _transform_langchain_message_content(content)
+        assert result == ["plain string", {"type": "text", "text": "dict text"}]
+
+    def test_transform_tuple_content(self):
+        """Test transformation of tuple content."""
+        content = (
+            {"type": "text", "text": "Message"},
+            {"type": "image", "base64": "data...", "mime_type": "image/png"},
+        )
+        result = _transform_langchain_message_content(content)
+        assert len(result) == 2
+        assert result[1] == {
+            "type": "blob",
+            "modality": "image",
+            "mime_type": "image/png",
+            "content": "data...",
+        }
+
+    def test_transform_list_with_legacy_image_url(self):
+        """Test transformation of list containing legacy image_url blocks."""
+        content = [
+            {"type": "text", "text": "Check this:"},
+            {
+                "type": "image_url",
+                "image_url": {"url": "data:image/jpeg;base64,/9j/4AAQ..."},
+            },
+        ]
+        result = _transform_langchain_message_content(content)
+        assert len(result) == 2
+        assert result[0] == {"type": "text", "text": "Check this:"}
+        assert result[1] == {
+            "type": "blob",
+            "modality": "image",
+            "mime_type": "image/jpeg",
+            "content": "/9j/4AAQ...",
+        }
diff --git a/tests/integrations/langgraph/test_langgraph.py b/tests/integrations/langgraph/test_langgraph.py
index 99ab216957..9ccd84309f 100644
--- a/tests/integrations/langgraph/test_langgraph.py
+++ b/tests/integrations/langgraph/test_langgraph.py
@@ -270,9 +270,8 @@ def original_invoke(self, *args, **kwargs):
             import json
 
             request_messages = json.loads(request_messages)
-        assert len(request_messages) == 2
-        assert request_messages[0]["content"] == "Hello, can you help me?"
-        assert request_messages[1]["content"] == "Of course! How can I assist you?"
+        assert len(request_messages) == 1
+        assert request_messages[0]["content"] == "Of course! How can I assist you?"
 
         response_text = invoke_span["data"][SPANDATA.GEN_AI_RESPONSE_TEXT]
         assert response_text == expected_assistant_response
@@ -1383,7 +1382,8 @@ def original_invoke(self, *args, **kwargs):
 
     parsed_messages = json.loads(messages_data)
     assert isinstance(parsed_messages, list)
-    assert len(parsed_messages) == 2
-    assert "small message 4" in str(parsed_messages[0])
-    assert "small message 5" in str(parsed_messages[1])
+    assert len(parsed_messages) == 1
+    assert "small message 5" in str(parsed_messages[0])
+
+    assert invoke_span["data"][SPANDATA.META_GEN_AI_ORIGINAL_INPUT_MESSAGES_LENGTH] == 5
     assert tx["_meta"]["spans"]["0"]["data"]["gen_ai.request.messages"][""]["len"] == 5
diff --git a/tests/integrations/litellm/test_litellm.py b/tests/integrations/litellm/test_litellm.py
index 1b925fb61f..06772342ab 100644
--- a/tests/integrations/litellm/test_litellm.py
+++ b/tests/integrations/litellm/test_litellm.py
@@ -1,3 +1,4 @@
+import base64
 import json
 import pytest
 import time
@@ -21,8 +22,10 @@ async def __call__(self, *args, **kwargs):
 import sentry_sdk
 from sentry_sdk import start_transaction
 from sentry_sdk.consts import OP, SPANDATA
+from sentry_sdk._types import BLOB_DATA_SUBSTITUTE
 from sentry_sdk.integrations.litellm import (
     LiteLLMIntegration,
+    _convert_message_parts,
     _input_callback,
     _success_callback,
     _failure_callback,
@@ -749,7 +752,246 @@ def test_litellm_message_truncation(sentry_init, capture_events):
 
     parsed_messages = json.loads(messages_data)
     assert isinstance(parsed_messages, list)
-    assert len(parsed_messages) == 2
-    assert "small message 4" in str(parsed_messages[0])
-    assert "small message 5" in str(parsed_messages[1])
+    assert len(parsed_messages) == 1
+    assert "small message 5" in str(parsed_messages[0])
+
+    assert chat_span["data"][SPANDATA.META_GEN_AI_ORIGINAL_INPUT_MESSAGES_LENGTH] == 5
     assert tx["_meta"]["spans"]["0"]["data"]["gen_ai.request.messages"][""]["len"] == 5
+
+
+IMAGE_DATA = b"fake_image_data_12345"
+IMAGE_B64 = base64.b64encode(IMAGE_DATA).decode("utf-8")
+IMAGE_DATA_URI = f"data:image/png;base64,{IMAGE_B64}"
+
+
+def test_binary_content_encoding_image_url(sentry_init, capture_events):
+    sentry_init(
+        integrations=[LiteLLMIntegration(include_prompts=True)],
+        traces_sample_rate=1.0,
+        send_default_pii=True,
+    )
+    events = capture_events()
+
+    messages = [
+        {
+            "role": "user",
+            "content": [
+                {"type": "text", "text": "Look at this image:"},
+                {
+                    "type": "image_url",
+                    "image_url": {"url": IMAGE_DATA_URI, "detail": "high"},
+                },
+            ],
+        }
+    ]
+    mock_response = MockCompletionResponse()
+
+    with start_transaction(name="litellm test"):
+        kwargs = {"model": "gpt-4-vision-preview", "messages": messages}
+        _input_callback(kwargs)
+        _success_callback(kwargs, mock_response, datetime.now(), datetime.now())
+
+    (event,) = events
+    (span,) = event["spans"]
+    messages_data = json.loads(span["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES])
+
+    blob_item = next(
+        (
+            item
+            for msg in messages_data
+            if "content" in msg
+            for item in msg["content"]
+            if item.get("type") == "blob"
+        ),
+        None,
+    )
+    assert blob_item is not None
+    assert blob_item["modality"] == "image"
+    assert blob_item["mime_type"] == "image/png"
+    assert (
+        IMAGE_B64 in blob_item["content"]
+        or blob_item["content"] == BLOB_DATA_SUBSTITUTE
+    )
+
+
+def test_binary_content_encoding_mixed_content(sentry_init, capture_events):
+    sentry_init(
+        integrations=[LiteLLMIntegration(include_prompts=True)],
+        traces_sample_rate=1.0,
+        send_default_pii=True,
+    )
+    events = capture_events()
+
+    messages = [
+        {
+            "role": "user",
+            "content": [
+                {"type": "text", "text": "Here is an image:"},
+                {
+                    "type": "image_url",
+                    "image_url": {"url": IMAGE_DATA_URI},
+                },
+                {"type": "text", "text": "What do you see?"},
+            ],
+        }
+    ]
+    mock_response = MockCompletionResponse()
+
+    with start_transaction(name="litellm test"):
+        kwargs = {"model": "gpt-4-vision-preview", "messages": messages}
+        _input_callback(kwargs)
+        _success_callback(kwargs, mock_response, datetime.now(), datetime.now())
+
+    (event,) = events
+    (span,) = event["spans"]
+    messages_data = json.loads(span["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES])
+
+    content_items = [
+        item for msg in messages_data if "content" in msg for item in msg["content"]
+    ]
+    assert any(item.get("type") == "text" for item in content_items)
+    assert any(item.get("type") == "blob" for item in content_items)
+
+
+def test_binary_content_encoding_uri_type(sentry_init, capture_events):
+    sentry_init(
+        integrations=[LiteLLMIntegration(include_prompts=True)],
+        traces_sample_rate=1.0,
+        send_default_pii=True,
+    )
+    events = capture_events()
+
+    messages = [
+        {
+            "role": "user",
+            "content": [
+                {
+                    "type": "image_url",
+                    "image_url": {"url": "https://example.com/image.jpg"},
+                }
+            ],
+        }
+    ]
+    mock_response = MockCompletionResponse()
+
+    with start_transaction(name="litellm test"):
+        kwargs = {"model": "gpt-4-vision-preview", "messages": messages}
+        _input_callback(kwargs)
+        _success_callback(kwargs, mock_response, datetime.now(), datetime.now())
+
+    (event,) = events
+    (span,) = event["spans"]
+    messages_data = json.loads(span["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES])
+
+    uri_item = next(
+        (
+            item
+            for msg in messages_data
+            if "content" in msg
+            for item in msg["content"]
+            if item.get("type") == "uri"
+        ),
+        None,
+    )
+    assert uri_item is not None
+    assert uri_item["uri"] == "https://example.com/image.jpg"
+
+
+def test_convert_message_parts_direct():
+    messages = [
+        {
+            "role": "user",
+            "content": [
+                {"type": "text", "text": "Hello"},
+                {
+                    "type": "image_url",
+                    "image_url": {"url": IMAGE_DATA_URI},
+                },
+            ],
+        }
+    ]
+    converted = _convert_message_parts(messages)
+    blob_item = next(
+        item for item in converted[0]["content"] if item.get("type") == "blob"
+    )
+    assert blob_item["modality"] == "image"
+    assert blob_item["mime_type"] == "image/png"
+    assert IMAGE_B64 in blob_item["content"]
+
+
+def test_convert_message_parts_does_not_mutate_original():
+    """Ensure _convert_message_parts does not mutate the original messages."""
+    original_url = IMAGE_DATA_URI
+    messages = [
+        {
+            "role": "user",
+            "content": [
+                {
+                    "type": "image_url",
+                    "image_url": {"url": original_url},
+                },
+            ],
+        }
+    ]
+    _convert_message_parts(messages)
+    # Original should be unchanged
+    assert messages[0]["content"][0]["type"] == "image_url"
+    assert messages[0]["content"][0]["image_url"]["url"] == original_url
+
+
+def test_convert_message_parts_data_url_without_base64():
+    """Data URLs without ;base64, marker are still inline data and should be blobs."""
+    messages = [
+        {
+            "role": "user",
+            "content": [
+                {
+                    "type": "image_url",
+                    "image_url": {"url": "data:image/png,rawdata"},
+                },
+            ],
+        }
+    ]
+    converted = _convert_message_parts(messages)
+    blob_item = converted[0]["content"][0]
+    # Data URIs (with or without base64 encoding) contain inline data and should be blobs
+    assert blob_item["type"] == "blob"
+    assert blob_item["modality"] == "image"
+    assert blob_item["mime_type"] == "image/png"
+    assert blob_item["content"] == "rawdata"
+
+
+def test_convert_message_parts_image_url_none():
+    """image_url being None should not crash."""
+    messages = [
+        {
+            "role": "user",
+            "content": [
+                {
+                    "type": "image_url",
+                    "image_url": None,
+                },
+            ],
+        }
+    ]
+    converted = _convert_message_parts(messages)
+    # Should return item unchanged
+    assert converted[0]["content"][0]["type"] == "image_url"
+
+
+def test_convert_message_parts_image_url_missing_url():
+    """image_url missing the url key should not crash."""
+    messages = [
+        {
+            "role": "user",
+            "content": [
+                {
+                    "type": "image_url",
+                    "image_url": {"detail": "high"},
+                },
+            ],
+        }
+    ]
+    converted = _convert_message_parts(messages)
+    # Should return item unchanged
+    assert converted[0]["content"][0]["type"] == "image_url"
diff --git a/tests/integrations/mcp/test_mcp.py b/tests/integrations/mcp/test_mcp.py
index 4415467cd7..715f9734ca 100644
--- a/tests/integrations/mcp/test_mcp.py
+++ b/tests/integrations/mcp/test_mcp.py
@@ -15,6 +15,9 @@
 that the integration properly instruments MCP handlers with Sentry spans.
 """
 
+import anyio
+import asyncio
+
 import pytest
 import json
 from unittest import mock
@@ -30,6 +33,8 @@ async def __call__(self, *args, **kwargs):
 
 from mcp.server.lowlevel import Server
 from mcp.server.lowlevel.server import request_ctx
+from mcp.types import GetPromptResult, PromptMessage, TextContent
+from mcp.server.lowlevel.helper_types import ReadResourceContents
 
 try:
     from mcp.server.lowlevel.server import request_ctx
@@ -40,6 +45,12 @@ async def __call__(self, *args, **kwargs):
 from sentry_sdk.consts import SPANDATA, OP
 from sentry_sdk.integrations.mcp import MCPIntegration
 
+from mcp.server.sse import SseServerTransport
+from mcp.server.streamable_http_manager import StreamableHTTPSessionManager
+from starlette.routing import Mount, Route
+from starlette.applications import Starlette
+from starlette.responses import Response
+
 
 @pytest.fixture(autouse=True)
 def reset_request_ctx():
@@ -60,47 +71,6 @@ def reset_request_ctx():
             pass
 
 
-# Mock MCP types and structures
-class MockURI:
-    """Mock URI object for resource testing"""
-
-    def __init__(self, uri_string):
-        self.scheme = uri_string.split("://")[0] if "://" in uri_string else ""
-        self.path = uri_string.split("://")[1] if "://" in uri_string else uri_string
-        self._uri_string = uri_string
-
-    def __str__(self):
-        return self._uri_string
-
-
-class MockRequestContext:
-    """Mock MCP request context"""
-
-    def __init__(self, request_id=None, session_id=None, transport="stdio"):
-        self.request_id = request_id
-        if transport in ("http", "sse"):
-            self.request = MockHTTPRequest(session_id, transport)
-        else:
-            self.request = None
-
-
-class MockHTTPRequest:
-    """Mock HTTP request for SSE/StreamableHTTP transport"""
-
-    def __init__(self, session_id=None, transport="http"):
-        self.headers = {}
-        self.query_params = {}
-
-        if transport == "sse":
-            # SSE transport uses query parameter
-            if session_id:
-                self.query_params["session_id"] = session_id
-        else:
-            # StreamableHTTP transport uses header
-            if session_id:
-                self.headers["mcp-session-id"] = session_id
-
-
 class MockTextContent:
     """Mock TextContent object"""
 
@@ -108,21 +78,6 @@ def __init__(self, text):
         self.text = text
 
 
-class MockPromptMessage:
-    """Mock PromptMessage object"""
-
-    def __init__(self, role, content_text):
-        self.role = role
-        self.content = MockTextContent(content_text)
-
-
-class MockGetPromptResult:
-    """Mock GetPromptResult object"""
-
-    def __init__(self, messages):
-        self.messages = messages
-
-
 def test_integration_patches_server(sentry_init):
     """Test that MCPIntegration patches the Server class"""
     # Get original methods before integration
@@ -141,12 +96,13 @@ def test_integration_patches_server(sentry_init):
     assert Server.read_resource is not original_read_resource
 
 
+@pytest.mark.asyncio
 @pytest.mark.parametrize(
     "send_default_pii, include_prompts",
     [(True, True), (True, False), (False, True), (False, False)],
 )
-def test_tool_handler_sync(
-    sentry_init, capture_events, send_default_pii, include_prompts
+async def test_tool_handler_stdio(
+    sentry_init, capture_events, send_default_pii, include_prompts, stdio
 ):
     """Test that synchronous tool handlers create proper spans"""
     sentry_init(
@@ -158,19 +114,25 @@ def test_tool_handler_sync(
 
     server = Server("test-server")
 
-    # Set up mock request context
-    mock_ctx = MockRequestContext(request_id="req-123", transport="stdio")
-    request_ctx.set(mock_ctx)
-
     @server.call_tool()
-    def test_tool(tool_name, arguments):
+    async def test_tool(tool_name, arguments):
         return {"result": "success", "value": 42}
 
     with start_transaction(name="mcp tx"):
-        # Call the tool handler
-        result = test_tool("calculate", {"x": 10, "y": 5})
+        result = await stdio(
+            server,
+            method="tools/call",
+            params={
+                "name": "calculate",
+                "arguments": {"x": 10, "y": 5},
+            },
+            request_id="req-123",
+        )
 
-    assert result == {"result": "success", "value": 42}
+    assert result.message.root.result["content"][0]["text"] == json.dumps(
+        {"result": "success", "value": 42},
+        indent=2,
+    )
 
     (tx,) = events
     assert tx["type"] == "transaction"
@@ -208,8 +170,13 @@ def test_tool(tool_name, arguments):
     "send_default_pii, include_prompts",
     [(True, True), (True, False), (False, True), (False, False)],
 )
-async def test_tool_handler_async(
-    sentry_init, capture_events, send_default_pii, include_prompts
+async def test_tool_handler_streamable_http(
+    sentry_init,
+    capture_events,
+    send_default_pii,
+    include_prompts,
+    json_rpc,
+    select_mcp_transactions,
 ):
     """Test that async tool handlers create proper spans"""
     sentry_init(
@@ -221,48 +188,75 @@ async def test_tool_handler_async(
 
     server = Server("test-server")
 
-    # Set up mock request context
-    mock_ctx = MockRequestContext(
-        request_id="req-456", session_id="session-789", transport="http"
+    session_manager = StreamableHTTPSessionManager(
+        app=server,
+        json_response=True,
+    )
+
+    app = Starlette(
+        routes=[
+            Mount("/mcp", app=session_manager.handle_request),
+        ],
+        lifespan=lambda app: session_manager.run(),
     )
-    request_ctx.set(mock_ctx)
 
     @server.call_tool()
     async def test_tool_async(tool_name, arguments):
-        return {"status": "completed"}
-
-    with start_transaction(name="mcp tx"):
-        result = await test_tool_async("process", {"data": "test"})
+        return [
+            TextContent(
+                type="text",
+                text=json.dumps({"status": "completed"}),
+            )
+        ]
 
-    assert result == {"status": "completed"}
+    session_id, result = json_rpc(
+        app,
+        method="tools/call",
+        params={
+            "name": "process",
+            "arguments": {
+                "data": "test",
+            },
+        },
+        request_id="req-456",
+    )
+    assert result.json()["result"]["content"][0]["text"] == json.dumps(
+        {"status": "completed"}
+    )
 
-    (tx,) = events
+    transactions = select_mcp_transactions(events)
+    assert len(transactions) == 1
+    tx = transactions[0]
     assert tx["type"] == "transaction"
-    assert len(tx["spans"]) == 1
 
-    span = tx["spans"][0]
-    assert span["op"] == OP.MCP_SERVER
-    assert span["description"] == "tools/call process"
-    assert span["origin"] == "auto.ai.mcp"
+    assert tx["contexts"]["trace"]["op"] == OP.MCP_SERVER
+    assert tx["transaction"] == "tools/call process"
+    assert tx["contexts"]["trace"]["origin"] == "auto.ai.mcp"
 
     # Check span data
-    assert span["data"][SPANDATA.MCP_TOOL_NAME] == "process"
-    assert span["data"][SPANDATA.MCP_METHOD_NAME] == "tools/call"
-    assert span["data"][SPANDATA.MCP_TRANSPORT] == "http"
-    assert span["data"][SPANDATA.MCP_REQUEST_ID] == "req-456"
-    assert span["data"][SPANDATA.MCP_SESSION_ID] == "session-789"
-    assert span["data"]["mcp.request.argument.data"] == '"test"'
+    assert tx["contexts"]["trace"]["data"][SPANDATA.MCP_TOOL_NAME] == "process"
+    assert tx["contexts"]["trace"]["data"][SPANDATA.MCP_METHOD_NAME] == "tools/call"
+    assert tx["contexts"]["trace"]["data"][SPANDATA.MCP_TRANSPORT] == "http"
+    assert tx["contexts"]["trace"]["data"][SPANDATA.MCP_REQUEST_ID] == "req-456"
+    assert tx["contexts"]["trace"]["data"][SPANDATA.MCP_SESSION_ID] == session_id
+    assert tx["contexts"]["trace"]["data"]["mcp.request.argument.data"] == '"test"'
 
     # Check PII-sensitive data
     if send_default_pii and include_prompts:
-        assert span["data"][SPANDATA.MCP_TOOL_RESULT_CONTENT] == json.dumps(
-            {"status": "completed"}
+        # TODO: Investigate why tool result is double-serialized.
+        assert tx["contexts"]["trace"]["data"][
+            SPANDATA.MCP_TOOL_RESULT_CONTENT
+        ] == json.dumps(
+            json.dumps(
+                {"status": "completed"},
+            )
         )
     else:
-        assert SPANDATA.MCP_TOOL_RESULT_CONTENT not in span["data"]
+        assert SPANDATA.MCP_TOOL_RESULT_CONTENT not in tx["contexts"]["trace"]["data"]
 
 
-def test_tool_handler_with_error(sentry_init, capture_events):
+@pytest.mark.asyncio
+async def test_tool_handler_with_error(sentry_init, capture_events, stdio):
     """Test that tool handler errors are captured properly"""
     sentry_init(
         integrations=[MCPIntegration()],
@@ -272,17 +266,24 @@ def test_tool_handler_with_error(sentry_init, capture_events):
 
     server = Server("test-server")
 
-    # Set up mock request context
-    mock_ctx = MockRequestContext(request_id="req-error", transport="stdio")
-    request_ctx.set(mock_ctx)
-
     @server.call_tool()
     def failing_tool(tool_name, arguments):
         raise ValueError("Tool execution failed")
 
     with start_transaction(name="mcp tx"):
-        with pytest.raises(ValueError):
-            failing_tool("bad_tool", {})
+        result = await stdio(
+            server,
+            method="tools/call",
+            params={
+                "name": "bad_tool",
+                "arguments": {},
+            },
+            request_id="req-error",
+        )
+
+        assert (
+            result.message.root.result["content"][0]["text"] == "Tool execution failed"
+        )
 
     # Should have error event and transaction
     assert len(events) == 2
@@ -304,12 +305,13 @@ def failing_tool(tool_name, arguments):
     assert span["tags"]["status"] == "internal_error"
 
 
+@pytest.mark.asyncio
 @pytest.mark.parametrize(
     "send_default_pii, include_prompts",
     [(True, True), (True, False), (False, True), (False, False)],
 )
-def test_prompt_handler_sync(
-    sentry_init, capture_events, send_default_pii, include_prompts
+async def test_prompt_handler_stdio(
+    sentry_init, capture_events, send_default_pii, include_prompts, stdio
 ):
     """Test that synchronous prompt handlers create proper spans"""
     sentry_init(
@@ -321,19 +323,34 @@ def test_prompt_handler_sync(
 
     server = Server("test-server")
 
-    # Set up mock request context
-    mock_ctx = MockRequestContext(request_id="req-prompt", transport="stdio")
-    request_ctx.set(mock_ctx)
-
     @server.get_prompt()
-    def test_prompt(name, arguments):
-        return MockGetPromptResult([MockPromptMessage("user", "Tell me about Python")])
+    async def test_prompt(name, arguments):
+        return GetPromptResult(
+            description="A helpful test prompt",
+            messages=[
+                PromptMessage(
+                    role="user",
+                    content=TextContent(type="text", text="Tell me about Python"),
+                ),
+            ],
+        )
 
     with start_transaction(name="mcp tx"):
-        result = test_prompt("code_help", {"language": "python"})
+        result = await stdio(
+            server,
+            method="prompts/get",
+            params={
+                "name": "code_help",
+                "arguments": {"language": "python"},
+            },
+            request_id="req-prompt",
+        )
 
-    assert result.messages[0].role == "user"
-    assert result.messages[0].content.text == "Tell me about Python"
+    assert result.message.root.result["messages"][0]["role"] == "user"
+    assert (
+        result.message.root.result["messages"][0]["content"]["text"]
+        == "Tell me about Python"
+    )
 
     (tx,) = events
     assert tx["type"] == "transaction"
@@ -372,8 +389,13 @@ def test_prompt(name, arguments):
     "send_default_pii, include_prompts",
     [(True, True), (True, False), (False, True), (False, False)],
 )
-async def test_prompt_handler_async(
-    sentry_init, capture_events, send_default_pii, include_prompts
+async def test_prompt_handler_streamable_http(
+    sentry_init,
+    capture_events,
+    send_default_pii,
+    include_prompts,
+    json_rpc,
+    select_mcp_transactions,
 ):
     """Test that async prompt handlers create proper spans"""
     sentry_init(
@@ -385,42 +407,70 @@ async def test_prompt_handler_async(
 
     server = Server("test-server")
 
-    # Set up mock request context
-    mock_ctx = MockRequestContext(
-        request_id="req-async-prompt", session_id="session-abc", transport="http"
+    session_manager = StreamableHTTPSessionManager(
+        app=server,
+        json_response=True,
+    )
+
+    app = Starlette(
+        routes=[
+            Mount("/mcp", app=session_manager.handle_request),
+        ],
+        lifespan=lambda app: session_manager.run(),
     )
-    request_ctx.set(mock_ctx)
 
     @server.get_prompt()
     async def test_prompt_async(name, arguments):
-        return MockGetPromptResult(
-            [
-                MockPromptMessage("system", "You are a helpful assistant"),
-                MockPromptMessage("user", "What is MCP?"),
-            ]
+        return GetPromptResult(
+            description="A helpful test prompt",
+            messages=[
+                PromptMessage(
+                    role="user",
+                    content=TextContent(
+                        type="text", text="You are a helpful assistant"
+                    ),
+                ),
+                PromptMessage(
+                    role="user", content=TextContent(type="text", text="What is MCP?")
+                ),
+            ],
         )
 
-    with start_transaction(name="mcp tx"):
-        result = await test_prompt_async("mcp_info", {})
-
-    assert len(result.messages) == 2
+    _, result = json_rpc(
+        app,
+        method="prompts/get",
+        params={
+            "name": "mcp_info",
+            "arguments": {},
+        },
+        request_id="req-async-prompt",
+    )
+    assert len(result.json()["result"]["messages"]) == 2
 
-    (tx,) = events
+    transactions = select_mcp_transactions(events)
+    assert len(transactions) == 1
+    tx = transactions[0]
     assert tx["type"] == "transaction"
-    assert len(tx["spans"]) == 1
 
-    span = tx["spans"][0]
-    assert span["op"] == OP.MCP_SERVER
-    assert span["description"] == "prompts/get mcp_info"
+    assert tx["contexts"]["trace"]["op"] == OP.MCP_SERVER
+    assert tx["transaction"] == "prompts/get mcp_info"
 
     # For multi-message prompts, count is always captured
-    assert span["data"][SPANDATA.MCP_PROMPT_RESULT_MESSAGE_COUNT] == 2
+    assert (
+        tx["contexts"]["trace"]["data"][SPANDATA.MCP_PROMPT_RESULT_MESSAGE_COUNT] == 2
+    )
     # Role/content are never captured for multi-message prompts (even with PII)
-    assert SPANDATA.MCP_PROMPT_RESULT_MESSAGE_ROLE not in span["data"]
-    assert SPANDATA.MCP_PROMPT_RESULT_MESSAGE_CONTENT not in span["data"]
+    assert (
+        SPANDATA.MCP_PROMPT_RESULT_MESSAGE_ROLE not in tx["contexts"]["trace"]["data"]
+    )
+    assert (
+        SPANDATA.MCP_PROMPT_RESULT_MESSAGE_CONTENT
+        not in tx["contexts"]["trace"]["data"]
+    )
 
 
-def test_prompt_handler_with_error(sentry_init, capture_events):
+@pytest.mark.asyncio
+async def test_prompt_handler_with_error(sentry_init, capture_events, stdio):
     """Test that prompt handler errors are captured"""
     sentry_init(
         integrations=[MCPIntegration()],
@@ -430,17 +480,22 @@ def test_prompt_handler_with_error(sentry_init, capture_events):
 
     server = Server("test-server")
 
-    # Set up mock request context
-    mock_ctx = MockRequestContext(request_id="req-error-prompt", transport="stdio")
-    request_ctx.set(mock_ctx)
-
     @server.get_prompt()
-    def failing_prompt(name, arguments):
+    async def failing_prompt(name, arguments):
         raise RuntimeError("Prompt not found")
 
     with start_transaction(name="mcp tx"):
-        with pytest.raises(RuntimeError):
-            failing_prompt("missing_prompt", {})
+        response = await stdio(
+            server,
+            method="prompts/get",
+            params={
+                "name": "code_help",
+                "arguments": {"language": "python"},
+            },
+            request_id="req-error-prompt",
+        )
+
+    assert response.message.root.error.message == "Prompt not found"
 
     # Should have error event and transaction
     assert len(events) == 2
@@ -450,7 +505,8 @@ def failing_prompt(name, arguments):
     assert error_event["exception"]["values"][0]["type"] == "RuntimeError"
 
 
-def test_resource_handler_sync(sentry_init, capture_events):
+@pytest.mark.asyncio
+async def test_resource_handler_stdio(sentry_init, capture_events, stdio):
     """Test that synchronous resource handlers create proper spans"""
     sentry_init(
         integrations=[MCPIntegration()],
@@ -460,19 +516,27 @@ def test_resource_handler_sync(sentry_init, capture_events):
 
     server = Server("test-server")
 
-    # Set up mock request context
-    mock_ctx = MockRequestContext(request_id="req-resource", transport="stdio")
-    request_ctx.set(mock_ctx)
-
     @server.read_resource()
-    def test_resource(uri):
-        return {"content": "file contents", "mime_type": "text/plain"}
+    async def test_resource(uri):
+        return [
+            ReadResourceContents(
+                content=json.dumps({"content": "file contents"}), mime_type="text/plain"
+            )
+        ]
 
     with start_transaction(name="mcp tx"):
-        uri = MockURI("file:///path/to/file.txt")
-        result = test_resource(uri)
+        result = await stdio(
+            server,
+            method="resources/read",
+            params={
+                "uri": "file:///path/to/file.txt",
+            },
+            request_id="req-resource",
+        )
 
-    assert result["content"] == "file contents"
+    assert result.message.root.result["contents"][0]["text"] == json.dumps(
+        {"content": "file contents"},
+    )
 
     (tx,) = events
     assert tx["type"] == "transaction"
@@ -494,7 +558,12 @@ def test_resource(uri):
 
 
 @pytest.mark.asyncio
-async def test_resource_handler_async(sentry_init, capture_events):
+async def test_resource_handler_streamble_http(
+    sentry_init,
+    capture_events,
+    json_rpc,
+    select_mcp_transactions,
+):
     """Test that async resource handlers create proper spans"""
     sentry_init(
         integrations=[MCPIntegration()],
@@ -504,36 +573,57 @@ async def test_resource_handler_async(sentry_init, capture_events):
 
     server = Server("test-server")
 
-    # Set up mock request context
-    mock_ctx = MockRequestContext(
-        request_id="req-async-resource", session_id="session-res", transport="http"
+    session_manager = StreamableHTTPSessionManager(
+        app=server,
+        json_response=True,
+    )
+
+    app = Starlette(
+        routes=[
+            Mount("/mcp", app=session_manager.handle_request),
+        ],
+        lifespan=lambda app: session_manager.run(),
     )
-    request_ctx.set(mock_ctx)
 
     @server.read_resource()
     async def test_resource_async(uri):
-        return {"data": "resource data"}
+        return [
+            ReadResourceContents(
+                content=json.dumps({"data": "resource data"}), mime_type="text/plain"
+            )
+        ]
 
-    with start_transaction(name="mcp tx"):
-        uri = MockURI("https://example.com/resource")
-        result = await test_resource_async(uri)
+    session_id, result = json_rpc(
+        app,
+        method="resources/read",
+        params={
+            "uri": "https://example.com/resource",
+        },
+        request_id="req-async-resource",
+    )
 
-    assert result["data"] == "resource data"
+    assert result.json()["result"]["contents"][0]["text"] == json.dumps(
+        {"data": "resource data"}
+    )
 
-    (tx,) = events
+    transactions = select_mcp_transactions(events)
+    assert len(transactions) == 1
+    tx = transactions[0]
     assert tx["type"] == "transaction"
-    assert len(tx["spans"]) == 1
 
-    span = tx["spans"][0]
-    assert span["op"] == OP.MCP_SERVER
-    assert span["description"] == "resources/read https://example.com/resource"
+    assert tx["contexts"]["trace"]["op"] == OP.MCP_SERVER
+    assert tx["transaction"] == "resources/read https://example.com/resource"
 
-    assert span["data"][SPANDATA.MCP_RESOURCE_URI] == "https://example.com/resource"
-    assert span["data"][SPANDATA.MCP_RESOURCE_PROTOCOL] == "https"
-    assert span["data"][SPANDATA.MCP_SESSION_ID] == "session-res"
+    assert (
+        tx["contexts"]["trace"]["data"][SPANDATA.MCP_RESOURCE_URI]
+        == "https://example.com/resource"
+    )
+    assert tx["contexts"]["trace"]["data"][SPANDATA.MCP_RESOURCE_PROTOCOL] == "https"
+    assert tx["contexts"]["trace"]["data"][SPANDATA.MCP_SESSION_ID] == session_id
 
 
-def test_resource_handler_with_error(sentry_init, capture_events):
+@pytest.mark.asyncio
+async def test_resource_handler_with_error(sentry_init, capture_events, stdio):
     """Test that resource handler errors are captured"""
     sentry_init(
         integrations=[MCPIntegration()],
@@ -543,18 +633,19 @@ def test_resource_handler_with_error(sentry_init, capture_events):
 
     server = Server("test-server")
 
-    # Set up mock request context
-    mock_ctx = MockRequestContext(request_id="req-error-resource", transport="stdio")
-    request_ctx.set(mock_ctx)
-
     @server.read_resource()
     def failing_resource(uri):
         raise FileNotFoundError("Resource not found")
 
     with start_transaction(name="mcp tx"):
-        with pytest.raises(FileNotFoundError):
-            uri = MockURI("file:///missing.txt")
-            failing_resource(uri)
+        await stdio(
+            server,
+            method="resources/read",
+            params={
+                "uri": "file:///missing.txt",
+            },
+            request_id="req-error-resource",
+        )
 
     # Should have error event and transaction
     assert len(events) == 2
@@ -564,12 +655,13 @@ def failing_resource(uri):
     assert error_event["exception"]["values"][0]["type"] == "FileNotFoundError"
 
 
+@pytest.mark.asyncio
 @pytest.mark.parametrize(
     "send_default_pii, include_prompts",
     [(True, True), (False, False)],
 )
-def test_tool_result_extraction_tuple(
-    sentry_init, capture_events, send_default_pii, include_prompts
+async def test_tool_result_extraction_tuple(
+    sentry_init, capture_events, send_default_pii, include_prompts, stdio
 ):
     """Test extraction of tool results from tuple format (UnstructuredContent, StructuredContent)"""
     sentry_init(
@@ -581,10 +673,6 @@ def test_tool_result_extraction_tuple(
 
     server = Server("test-server")
 
-    # Set up mock request context
-    mock_ctx = MockRequestContext(request_id="req-tuple", transport="stdio")
-    request_ctx.set(mock_ctx)
-
     @server.call_tool()
     def test_tool_tuple(tool_name, arguments):
         # Return CombinationContent: (UnstructuredContent, StructuredContent)
@@ -593,7 +681,15 @@ def test_tool_tuple(tool_name, arguments):
         return (unstructured, structured)
 
     with start_transaction(name="mcp tx"):
-        test_tool_tuple("combo_tool", {})
+        await stdio(
+            server,
+            method="tools/call",
+            params={
+                "name": "calculate",
+                "arguments": {},
+            },
+            request_id="req-tuple",
+        )
 
     (tx,) = events
     span = tx["spans"][0]
@@ -612,12 +708,13 @@ def test_tool_tuple(tool_name, arguments):
         assert SPANDATA.MCP_TOOL_RESULT_CONTENT_COUNT not in span["data"]
 
 
+@pytest.mark.asyncio
 @pytest.mark.parametrize(
     "send_default_pii, include_prompts",
     [(True, True), (False, False)],
 )
-def test_tool_result_extraction_unstructured(
-    sentry_init, capture_events, send_default_pii, include_prompts
+async def test_tool_result_extraction_unstructured(
+    sentry_init, capture_events, send_default_pii, include_prompts, stdio
 ):
     """Test extraction of tool results from UnstructuredContent (list of content blocks)"""
     sentry_init(
@@ -629,10 +726,6 @@ def test_tool_result_extraction_unstructured(
 
     server = Server("test-server")
 
-    # Set up mock request context
-    mock_ctx = MockRequestContext(request_id="req-unstructured", transport="stdio")
-    request_ctx.set(mock_ctx)
-
     @server.call_tool()
     def test_tool_unstructured(tool_name, arguments):
         # Return UnstructuredContent as list of content blocks
@@ -642,7 +735,15 @@ def test_tool_unstructured(tool_name, arguments):
         ]
 
     with start_transaction(name="mcp tx"):
-        test_tool_unstructured("text_tool", {})
+        await stdio(
+            server,
+            method="tools/call",
+            params={
+                "name": "text_tool",
+                "arguments": {},
+            },
+            request_id="req-unstructured",
+        )
 
     (tx,) = events
     span = tx["spans"][0]
@@ -656,44 +757,8 @@ def test_tool_unstructured(tool_name, arguments):
         assert SPANDATA.MCP_TOOL_RESULT_CONTENT not in span["data"]
 
 
-def test_request_context_no_context(sentry_init, capture_events):
-    """Test handling when no request context is available"""
-    sentry_init(
-        integrations=[MCPIntegration()],
-        traces_sample_rate=1.0,
-    )
-    events = capture_events()
-
-    server = Server("test-server")
-
-    # Clear request context (simulating no context available)
-    # This will cause a LookupError when trying to get context
-    request_ctx.set(None)
-
-    @server.call_tool()
-    def test_tool_no_ctx(tool_name, arguments):
-        return {"result": "ok"}
-
-    with start_transaction(name="mcp tx"):
-        # This should work even without request context
-        try:
-            test_tool_no_ctx("tool", {})
-        except LookupError:
-            # If it raises LookupError, that's expected when context is truly missing
-            pass
-
-    # Should still create span even if context is missing
-    (tx,) = events
-    span = tx["spans"][0]
-
-    # Transport defaults to "pipe" when no context
-    assert span["data"][SPANDATA.MCP_TRANSPORT] == "stdio"
-    # Request ID and Session ID should not be present
-    assert SPANDATA.MCP_REQUEST_ID not in span["data"]
-    assert SPANDATA.MCP_SESSION_ID not in span["data"]
-
-
-def test_span_origin(sentry_init, capture_events):
+@pytest.mark.asyncio
+async def test_span_origin(sentry_init, capture_events, stdio):
     """Test that span origin is set correctly"""
     sentry_init(
         integrations=[MCPIntegration()],
@@ -703,16 +768,20 @@ def test_span_origin(sentry_init, capture_events):
 
     server = Server("test-server")
 
-    # Set up mock request context
-    mock_ctx = MockRequestContext(request_id="req-origin", transport="stdio")
-    request_ctx.set(mock_ctx)
-
     @server.call_tool()
     def test_tool(tool_name, arguments):
         return {"result": "test"}
 
     with start_transaction(name="mcp tx"):
-        test_tool("origin_test", {})
+        await stdio(
+            server,
+            method="tools/call",
+            params={
+                "name": "calculate",
+                "arguments": {"x": 10, "y": 5},
+            },
+            request_id="req-origin",
+        )
 
     (tx,) = events
 
@@ -720,7 +789,8 @@ def test_tool(tool_name, arguments):
     assert tx["spans"][0]["origin"] == "auto.ai.mcp"
 
 
-def test_multiple_handlers(sentry_init, capture_events):
+@pytest.mark.asyncio
+async def test_multiple_handlers(sentry_init, capture_events, stdio):
     """Test that multiple handler calls create multiple spans"""
     sentry_init(
         integrations=[MCPIntegration()],
@@ -730,10 +800,6 @@ def test_multiple_handlers(sentry_init, capture_events):
 
     server = Server("test-server")
 
-    # Set up mock request context
-    mock_ctx = MockRequestContext(request_id="req-multi", transport="stdio")
-    request_ctx.set(mock_ctx)
-
     @server.call_tool()
     def tool1(tool_name, arguments):
         return {"result": "tool1"}
@@ -744,12 +810,45 @@ def tool2(tool_name, arguments):
 
     @server.get_prompt()
     def prompt1(name, arguments):
-        return MockGetPromptResult([MockPromptMessage("user", "Test prompt")])
+        return GetPromptResult(
+            description="A test prompt",
+            messages=[
+                PromptMessage(
+                    role="user", content=TextContent(type="text", text="Test prompt")
+                )
+            ],
+        )
 
     with start_transaction(name="mcp tx"):
-        tool1("tool_a", {})
-        tool2("tool_b", {})
-        prompt1("prompt_a", {})
+        await stdio(
+            server,
+            method="tools/call",
+            params={
+                "name": "tool_a",
+                "arguments": {},
+            },
+            request_id="req-multi",
+        )
+
+        await stdio(
+            server,
+            method="tools/call",
+            params={
+                "name": "tool_b",
+                "arguments": {},
+            },
+            request_id="req-multi",
+        )
+
+        await stdio(
+            server,
+            method="prompts/get",
+            params={
+                "name": "prompt_a",
+                "arguments": {},
+            },
+            request_id="req-multi",
+        )
 
     (tx,) = events
     assert tx["type"] == "transaction"
@@ -765,12 +864,13 @@ def prompt1(name, arguments):
     assert "prompts/get prompt_a" in span_descriptions
 
 
+@pytest.mark.asyncio
 @pytest.mark.parametrize(
     "send_default_pii, include_prompts",
     [(True, True), (False, False)],
 )
-def test_prompt_with_dict_result(
-    sentry_init, capture_events, send_default_pii, include_prompts
+async def test_prompt_with_dict_result(
+    sentry_init, capture_events, send_default_pii, include_prompts, stdio
 ):
     """Test prompt handler with dict result instead of GetPromptResult object"""
     sentry_init(
@@ -782,10 +882,6 @@ def test_prompt_with_dict_result(
 
     server = Server("test-server")
 
-    # Set up mock request context
-    mock_ctx = MockRequestContext(request_id="req-dict-prompt", transport="stdio")
-    request_ctx.set(mock_ctx)
-
     @server.get_prompt()
     def test_prompt_dict(name, arguments):
         # Return dict format instead of GetPromptResult object
@@ -796,7 +892,15 @@ def test_prompt_dict(name, arguments):
         }
 
     with start_transaction(name="mcp tx"):
-        test_prompt_dict("dict_prompt", {})
+        await stdio(
+            server,
+            method="prompts/get",
+            params={
+                "name": "dict_prompt",
+                "arguments": {},
+            },
+            request_id="req-dict-prompt",
+        )
 
     (tx,) = events
     span = tx["spans"][0]
@@ -816,37 +920,8 @@ def test_prompt_dict(name, arguments):
         assert SPANDATA.MCP_PROMPT_RESULT_MESSAGE_CONTENT not in span["data"]
 
 
-def test_resource_without_protocol(sentry_init, capture_events):
-    """Test resource handler with URI without protocol scheme"""
-    sentry_init(
-        integrations=[MCPIntegration()],
-        traces_sample_rate=1.0,
-    )
-    events = capture_events()
-
-    server = Server("test-server")
-
-    # Set up mock request context
-    mock_ctx = MockRequestContext(request_id="req-no-proto", transport="stdio")
-    request_ctx.set(mock_ctx)
-
-    @server.read_resource()
-    def test_resource(uri):
-        return {"data": "test"}
-
-    with start_transaction(name="mcp tx"):
-        # URI without protocol
-        test_resource("simple-path")
-
-    (tx,) = events
-    span = tx["spans"][0]
-
-    assert span["data"][SPANDATA.MCP_RESOURCE_URI] == "simple-path"
-    # No protocol should be set
-    assert SPANDATA.MCP_RESOURCE_PROTOCOL not in span["data"]
-
-
-def test_tool_with_complex_arguments(sentry_init, capture_events):
+@pytest.mark.asyncio
+async def test_tool_with_complex_arguments(sentry_init, capture_events, stdio):
     """Test tool handler with complex nested arguments"""
     sentry_init(
         integrations=[MCPIntegration()],
@@ -856,10 +931,6 @@ def test_tool_with_complex_arguments(sentry_init, capture_events):
 
     server = Server("test-server")
 
-    # Set up mock request context
-    mock_ctx = MockRequestContext(request_id="req-complex", transport="stdio")
-    request_ctx.set(mock_ctx)
-
     @server.call_tool()
     def test_tool_complex(tool_name, arguments):
         return {"processed": True}
@@ -870,7 +941,15 @@ def test_tool_complex(tool_name, arguments):
             "string": "test",
             "number": 42,
         }
-        test_tool_complex("complex_tool", complex_args)
+        await stdio(
+            server,
+            method="tools/call",
+            params={
+                "name": "complex_tool",
+                "arguments": complex_args,
+            },
+            request_id="req-complex",
+        )
 
     (tx,) = events
     span = tx["spans"][0]
@@ -884,8 +963,8 @@ def test_tool_complex(tool_name, arguments):
 
 
 @pytest.mark.asyncio
-async def test_async_handlers_mixed(sentry_init, capture_events):
-    """Test mixing sync and async handlers in the same transaction"""
+async def test_sse_transport_detection(sentry_init, capture_events, json_rpc_sse):
+    """Test that SSE transport is correctly detected via query parameter"""
     sentry_init(
         integrations=[MCPIntegration()],
         traces_sample_rate=1.0,
@@ -893,68 +972,75 @@ async def test_async_handlers_mixed(sentry_init, capture_events):
     events = capture_events()
 
     server = Server("test-server")
+    sse = SseServerTransport("/messages/")
 
-    # Set up mock request context
-    mock_ctx = MockRequestContext(request_id="req-mixed", transport="stdio")
-    request_ctx.set(mock_ctx)
-
-    @server.call_tool()
-    def sync_tool(tool_name, arguments):
-        return {"type": "sync"}
-
-    @server.call_tool()
-    async def async_tool(tool_name, arguments):
-        return {"type": "async"}
-
-    with start_transaction(name="mcp tx"):
-        sync_result = sync_tool("sync", {})
-        async_result = await async_tool("async", {})
-
-    assert sync_result["type"] == "sync"
-    assert async_result["type"] == "async"
-
-    (tx,) = events
-    assert len(tx["spans"]) == 2
+    sse_connection_closed = asyncio.Event()
 
-    # Both should be instrumented correctly
-    assert all(span["op"] == OP.MCP_SERVER for span in tx["spans"])
+    async def handle_sse(request):
+        async with sse.connect_sse(
+            request.scope, request.receive, request._send
+        ) as streams:
+            async with anyio.create_task_group() as tg:
 
+                async def run_server():
+                    await server.run(
+                        streams[0], streams[1], server.create_initialization_options()
+                    )
 
-def test_sse_transport_detection(sentry_init, capture_events):
-    """Test that SSE transport is correctly detected via query parameter"""
-    sentry_init(
-        integrations=[MCPIntegration()],
-        traces_sample_rate=1.0,
-    )
-    events = capture_events()
+                tg.start_soon(run_server)
 
-    server = Server("test-server")
+        sse_connection_closed.set()
+        return Response()
 
-    # Set up mock request context with SSE transport
-    mock_ctx = MockRequestContext(
-        request_id="req-sse", session_id="session-sse-123", transport="sse"
+    app = Starlette(
+        routes=[
+            Route("/sse", endpoint=handle_sse, methods=["GET"]),
+            Mount("/messages/", app=sse.handle_post_message),
+        ],
     )
-    request_ctx.set(mock_ctx)
 
     @server.call_tool()
-    def test_tool(tool_name, arguments):
+    async def test_tool(tool_name, arguments):
         return {"result": "success"}
 
-    with start_transaction(name="mcp tx"):
-        result = test_tool("sse_tool", {})
+    keep_sse_alive = asyncio.Event()
+    app_task, session_id, result = await json_rpc_sse(
+        app,
+        method="tools/call",
+        params={
+            "name": "sse_tool",
+            "arguments": {},
+        },
+        request_id="req-sse",
+        keep_sse_alive=keep_sse_alive,
+    )
 
-    assert result == {"result": "success"}
+    await sse_connection_closed.wait()
+    await app_task
 
-    (tx,) = events
+    assert result["result"]["structuredContent"] == {"result": "success"}
+
+    transactions = [
+        event
+        for event in events
+        if event["type"] == "transaction" and event["transaction"] == "/sse"
+    ]
+    assert len(transactions) == 1
+    tx = transactions[0]
     span = tx["spans"][0]
 
     # Check that SSE transport is detected
     assert span["data"][SPANDATA.MCP_TRANSPORT] == "sse"
     assert span["data"][SPANDATA.NETWORK_TRANSPORT] == "tcp"
-    assert span["data"][SPANDATA.MCP_SESSION_ID] == "session-sse-123"
+    assert span["data"][SPANDATA.MCP_SESSION_ID] == session_id
 
 
-def test_streamable_http_transport_detection(sentry_init, capture_events):
+def test_streamable_http_transport_detection(
+    sentry_init,
+    capture_events,
+    json_rpc,
+    select_mcp_transactions,
+):
     """Test that StreamableHTTP transport is correctly detected via header"""
     sentry_init(
         integrations=[MCPIntegration()],
@@ -964,31 +1050,52 @@ def test_streamable_http_transport_detection(sentry_init, capture_events):
 
     server = Server("test-server")
 
-    # Set up mock request context with StreamableHTTP transport
-    mock_ctx = MockRequestContext(
-        request_id="req-http", session_id="session-http-456", transport="http"
+    session_manager = StreamableHTTPSessionManager(
+        app=server,
+        json_response=True,
     )
-    request_ctx.set(mock_ctx)
 
-    @server.call_tool()
-    def test_tool(tool_name, arguments):
-        return {"result": "success"}
+    app = Starlette(
+        routes=[
+            Mount("/mcp", app=session_manager.handle_request),
+        ],
+        lifespan=lambda app: session_manager.run(),
+    )
 
-    with start_transaction(name="mcp tx"):
-        result = test_tool("http_tool", {})
+    @server.call_tool()
+    async def test_tool(tool_name, arguments):
+        return [
+            TextContent(
+                type="text",
+                text=json.dumps({"status": "success"}),
+            )
+        ]
 
-    assert result == {"result": "success"}
+    session_id, result = json_rpc(
+        app,
+        method="tools/call",
+        params={
+            "name": "http_tool",
+            "arguments": {},
+        },
+        request_id="req-http",
+    )
+    assert result.json()["result"]["content"][0]["text"] == json.dumps(
+        {"status": "success"}
+    )
 
-    (tx,) = events
-    span = tx["spans"][0]
+    transactions = select_mcp_transactions(events)
+    assert len(transactions) == 1
+    tx = transactions[0]
 
     # Check that HTTP transport is detected
-    assert span["data"][SPANDATA.MCP_TRANSPORT] == "http"
-    assert span["data"][SPANDATA.NETWORK_TRANSPORT] == "tcp"
-    assert span["data"][SPANDATA.MCP_SESSION_ID] == "session-http-456"
+    assert tx["contexts"]["trace"]["data"][SPANDATA.MCP_TRANSPORT] == "http"
+    assert tx["contexts"]["trace"]["data"][SPANDATA.NETWORK_TRANSPORT] == "tcp"
+    assert tx["contexts"]["trace"]["data"][SPANDATA.MCP_SESSION_ID] == session_id
 
 
-def test_stdio_transport_detection(sentry_init, capture_events):
+@pytest.mark.asyncio
+async def test_stdio_transport_detection(sentry_init, capture_events, stdio):
     """Test that stdio transport is correctly detected when no HTTP request"""
     sentry_init(
         integrations=[MCPIntegration()],
@@ -998,18 +1105,22 @@ def test_stdio_transport_detection(sentry_init, capture_events):
 
     server = Server("test-server")
 
-    # Set up mock request context with stdio transport (no HTTP request)
-    mock_ctx = MockRequestContext(request_id="req-stdio", transport="stdio")
-    request_ctx.set(mock_ctx)
-
     @server.call_tool()
-    def test_tool(tool_name, arguments):
+    async def test_tool(tool_name, arguments):
         return {"result": "success"}
 
     with start_transaction(name="mcp tx"):
-        result = test_tool("stdio_tool", {})
+        result = await stdio(
+            server,
+            method="tools/call",
+            params={
+                "name": "stdio_tool",
+                "arguments": {},
+            },
+            request_id="req-stdio",
+        )
 
-    assert result == {"result": "success"}
+    assert result.message.root.result["structuredContent"] == {"result": "success"}
 
     (tx,) = events
     span = tx["spans"][0]
diff --git a/tests/integrations/openai/test_openai.py b/tests/integrations/openai/test_openai.py
index 814289c887..3581a14bd7 100644
--- a/tests/integrations/openai/test_openai.py
+++ b/tests/integrations/openai/test_openai.py
@@ -9,8 +9,10 @@
     NOT_GIVEN = None
 try:
     from openai import omit
+    from openai import Omit
 except ImportError:
     omit = None
+    Omit = None
 
 from openai import AsyncOpenAI, OpenAI, AsyncStream, Stream, OpenAIError
 from openai.types import CompletionUsage, CreateEmbeddingResponse, Embedding
@@ -44,9 +46,9 @@
     OpenAIIntegration,
     _calculate_token_usage,
 )
-from sentry_sdk.ai.utils import MAX_GEN_AI_MESSAGE_BYTES
 from sentry_sdk._types import AnnotatedValue
 from sentry_sdk.serializer import serialize
+from sentry_sdk.utils import safe_serialize
 
 from unittest import mock  # python 3.3 and above
 
@@ -129,9 +131,13 @@ async def async_iterator(values):
 
 @pytest.mark.parametrize(
     "send_default_pii, include_prompts",
-    [(True, True), (True, False), (False, True), (False, False)],
+    [
+        (True, False),
+        (False, True),
+        (False, False),
+    ],
 )
-def test_nonstreaming_chat_completion(
+def test_nonstreaming_chat_completion_no_prompts(
     sentry_init, capture_events, send_default_pii, include_prompts
 ):
     sentry_init(
@@ -147,7 +153,11 @@ def test_nonstreaming_chat_completion(
     with start_transaction(name="openai tx"):
         response = (
             client.chat.completions.create(
-                model="some-model", messages=[{"role": "system", "content": "hello"}]
+                model="some-model",
+                messages=[
+                    {"role": "system", "content": "You are a helpful assistant."},
+                    {"role": "user", "content": "hello"},
+                ],
             )
             .choices[0]
             .message.content
@@ -159,12 +169,92 @@ def test_nonstreaming_chat_completion(
     span = tx["spans"][0]
     assert span["op"] == "gen_ai.chat"
 
-    if send_default_pii and include_prompts:
-        assert "hello" in span["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES]
-        assert "the model response" in span["data"][SPANDATA.GEN_AI_RESPONSE_TEXT]
+    assert SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS not in span["data"]
+    assert SPANDATA.GEN_AI_REQUEST_MESSAGES not in span["data"]
+    assert SPANDATA.GEN_AI_RESPONSE_TEXT not in span["data"]
+
+    assert span["data"]["gen_ai.usage.output_tokens"] == 10
+    assert span["data"]["gen_ai.usage.input_tokens"] == 20
+    assert span["data"]["gen_ai.usage.total_tokens"] == 30
+
+
+@pytest.mark.parametrize(
+    "messages",
+    [
+        pytest.param(
+            [
+                {
+                    "role": "system",
+                    "content": "You are a helpful assistant.",
+                },
+                {"role": "user", "content": "hello"},
+            ],
+            id="blocks",
+        ),
+        pytest.param(
+            [
+                {
+                    "role": "system",
+                    "content": [
+                        {"type": "text", "text": "You are a helpful assistant."},
+                        {"type": "text", "text": "Be concise and clear."},
+                    ],
+                },
+                {"role": "user", "content": "hello"},
+            ],
+            id="parts",
+        ),
+    ],
+)
+def test_nonstreaming_chat_completion(sentry_init, capture_events, messages, request):
+    sentry_init(
+        integrations=[OpenAIIntegration(include_prompts=True)],
+        traces_sample_rate=1.0,
+        send_default_pii=True,
+    )
+    events = capture_events()
+
+    client = OpenAI(api_key="z")
+    client.chat.completions._post = mock.Mock(return_value=EXAMPLE_CHAT_COMPLETION)
+
+    with start_transaction(name="openai tx"):
+        response = (
+            client.chat.completions.create(
+                model="some-model",
+                messages=messages,
+            )
+            .choices[0]
+            .message.content
+        )
+
+    assert response == "the model response"
+    tx = events[0]
+    assert tx["type"] == "transaction"
+    span = tx["spans"][0]
+    assert span["op"] == "gen_ai.chat"
+
+    param_id = request.node.callspec.id
+    if "blocks" in param_id:
+        assert json.loads(span["data"][SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS]) == [
+            {
+                "type": "text",
+                "content": "You are a helpful assistant.",
+            }
+        ]
     else:
-        assert SPANDATA.GEN_AI_REQUEST_MESSAGES not in span["data"]
-        assert SPANDATA.GEN_AI_RESPONSE_TEXT not in span["data"]
+        assert json.loads(span["data"][SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS]) == [
+            {
+                "type": "text",
+                "content": "You are a helpful assistant.",
+            },
+            {
+                "type": "text",
+                "content": "Be concise and clear.",
+            },
+        ]
+
+    assert "hello" in span["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES]
+    assert "the model response" in span["data"][SPANDATA.GEN_AI_RESPONSE_TEXT]
 
     assert span["data"]["gen_ai.usage.output_tokens"] == 10
     assert span["data"]["gen_ai.usage.input_tokens"] == 20
@@ -174,9 +264,13 @@ def test_nonstreaming_chat_completion(
 @pytest.mark.asyncio
 @pytest.mark.parametrize(
     "send_default_pii, include_prompts",
-    [(True, True), (True, False), (False, True), (False, False)],
+    [
+        (True, False),
+        (False, True),
+        (False, False),
+    ],
 )
-async def test_nonstreaming_chat_completion_async(
+async def test_nonstreaming_chat_completion_async_no_prompts(
     sentry_init, capture_events, send_default_pii, include_prompts
 ):
     sentry_init(
@@ -186,12 +280,80 @@ async def test_nonstreaming_chat_completion_async(
     )
     events = capture_events()
 
+    client = AsyncOpenAI(api_key="z")
+    client.chat.completions._post = mock.AsyncMock(return_value=EXAMPLE_CHAT_COMPLETION)
+
+    with start_transaction(name="openai tx"):
+        response = await client.chat.completions.create(
+            model="some-model",
+            messages=[
+                {"role": "system", "content": "You are a helpful assistant."},
+                {"role": "user", "content": "hello"},
+            ],
+        )
+        response = response.choices[0].message.content
+
+    assert response == "the model response"
+    tx = events[0]
+    assert tx["type"] == "transaction"
+    span = tx["spans"][0]
+    assert span["op"] == "gen_ai.chat"
+
+    assert SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS not in span["data"]
+    assert SPANDATA.GEN_AI_REQUEST_MESSAGES not in span["data"]
+    assert SPANDATA.GEN_AI_RESPONSE_TEXT not in span["data"]
+
+    assert span["data"]["gen_ai.usage.output_tokens"] == 10
+    assert span["data"]["gen_ai.usage.input_tokens"] == 20
+    assert span["data"]["gen_ai.usage.total_tokens"] == 30
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize(
+    "messages",
+    [
+        pytest.param(
+            [
+                {
+                    "role": "system",
+                    "content": "You are a helpful assistant.",
+                },
+                {"role": "user", "content": "hello"},
+            ],
+            id="blocks",
+        ),
+        pytest.param(
+            [
+                {
+                    "role": "system",
+                    "content": [
+                        {"type": "text", "text": "You are a helpful assistant."},
+                        {"type": "text", "text": "Be concise and clear."},
+                    ],
+                },
+                {"role": "user", "content": "hello"},
+            ],
+            id="parts",
+        ),
+    ],
+)
+async def test_nonstreaming_chat_completion_async(
+    sentry_init, capture_events, messages, request
+):
+    sentry_init(
+        integrations=[OpenAIIntegration(include_prompts=True)],
+        traces_sample_rate=1.0,
+        send_default_pii=True,
+    )
+    events = capture_events()
+
     client = AsyncOpenAI(api_key="z")
     client.chat.completions._post = AsyncMock(return_value=EXAMPLE_CHAT_COMPLETION)
 
     with start_transaction(name="openai tx"):
         response = await client.chat.completions.create(
-            model="some-model", messages=[{"role": "system", "content": "hello"}]
+            model="some-model",
+            messages=messages,
         )
         response = response.choices[0].message.content
 
@@ -201,12 +363,28 @@ async def test_nonstreaming_chat_completion_async(
     span = tx["spans"][0]
     assert span["op"] == "gen_ai.chat"
 
-    if send_default_pii and include_prompts:
-        assert "hello" in span["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES]
-        assert "the model response" in span["data"][SPANDATA.GEN_AI_RESPONSE_TEXT]
+    param_id = request.node.callspec.id
+    if "blocks" in param_id:
+        assert json.loads(span["data"][SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS]) == [
+            {
+                "type": "text",
+                "content": "You are a helpful assistant.",
+            }
+        ]
     else:
-        assert SPANDATA.GEN_AI_REQUEST_MESSAGES not in span["data"]
-        assert SPANDATA.GEN_AI_RESPONSE_TEXT not in span["data"]
+        assert json.loads(span["data"][SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS]) == [
+            {
+                "type": "text",
+                "content": "You are a helpful assistant.",
+            },
+            {
+                "type": "text",
+                "content": "Be concise and clear.",
+            },
+        ]
+
+    assert "hello" in span["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES]
+    assert "the model response" in span["data"][SPANDATA.GEN_AI_RESPONSE_TEXT]
 
     assert span["data"]["gen_ai.usage.output_tokens"] == 10
     assert span["data"]["gen_ai.usage.input_tokens"] == 20
@@ -225,9 +403,13 @@ def tiktoken_encoding_if_installed():
 # noinspection PyTypeChecker
 @pytest.mark.parametrize(
     "send_default_pii, include_prompts",
-    [(True, True), (True, False), (False, True), (False, False)],
+    [
+        (True, False),
+        (False, True),
+        (False, False),
+    ],
 )
-def test_streaming_chat_completion(
+def test_streaming_chat_completion_no_prompts(
     sentry_init, capture_events, send_default_pii, include_prompts
 ):
     sentry_init(
@@ -283,7 +465,11 @@ def test_streaming_chat_completion(
     client.chat.completions._post = mock.Mock(return_value=returned_stream)
     with start_transaction(name="openai tx"):
         response_stream = client.chat.completions.create(
-            model="some-model", messages=[{"role": "system", "content": "hello"}]
+            model="some-model",
+            messages=[
+                {"role": "system", "content": "You are a helpful assistant."},
+                {"role": "user", "content": "hello"},
+            ],
         )
         response_string = "".join(
             map(lambda x: x.choices[0].delta.content, response_stream)
@@ -294,19 +480,149 @@ def test_streaming_chat_completion(
     span = tx["spans"][0]
     assert span["op"] == "gen_ai.chat"
 
-    if send_default_pii and include_prompts:
-        assert "hello" in span["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES]
-        assert "hello world" in span["data"][SPANDATA.GEN_AI_RESPONSE_TEXT]
-    else:
-        assert SPANDATA.GEN_AI_REQUEST_MESSAGES not in span["data"]
-        assert SPANDATA.GEN_AI_RESPONSE_TEXT not in span["data"]
+    assert SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS not in span["data"]
+    assert SPANDATA.GEN_AI_REQUEST_MESSAGES not in span["data"]
+    assert SPANDATA.GEN_AI_RESPONSE_TEXT not in span["data"]
 
     try:
         import tiktoken  # type: ignore # noqa # pylint: disable=unused-import
 
         assert span["data"]["gen_ai.usage.output_tokens"] == 2
-        assert span["data"]["gen_ai.usage.input_tokens"] == 1
-        assert span["data"]["gen_ai.usage.total_tokens"] == 3
+        assert span["data"]["gen_ai.usage.input_tokens"] == 7
+        assert span["data"]["gen_ai.usage.total_tokens"] == 9
+    except ImportError:
+        pass  # if tiktoken is not installed, we can't guarantee token usage will be calculated properly
+
+
+# noinspection PyTypeChecker
+@pytest.mark.parametrize(
+    "messages",
+    [
+        pytest.param(
+            [
+                {
+                    "role": "system",
+                    "content": "You are a helpful assistant.",
+                },
+                {"role": "user", "content": "hello"},
+            ],
+            id="blocks",
+        ),
+        pytest.param(
+            [
+                {
+                    "role": "system",
+                    "content": [
+                        {"type": "text", "text": "You are a helpful assistant."},
+                        {"type": "text", "text": "Be concise and clear."},
+                    ],
+                },
+                {"role": "user", "content": "hello"},
+            ],
+            id="parts",
+        ),
+    ],
+)
+def test_streaming_chat_completion(sentry_init, capture_events, messages, request):
+    sentry_init(
+        integrations=[
+            OpenAIIntegration(
+                include_prompts=True,
+                tiktoken_encoding_name=tiktoken_encoding_if_installed(),
+            )
+        ],
+        traces_sample_rate=1.0,
+        send_default_pii=True,
+    )
+    events = capture_events()
+
+    client = OpenAI(api_key="z")
+    returned_stream = Stream(cast_to=None, response=None, client=client)
+    returned_stream._iterator = [
+        ChatCompletionChunk(
+            id="1",
+            choices=[
+                DeltaChoice(
+                    index=0, delta=ChoiceDelta(content="hel"), finish_reason=None
+                )
+            ],
+            created=100000,
+            model="model-id",
+            object="chat.completion.chunk",
+        ),
+        ChatCompletionChunk(
+            id="1",
+            choices=[
+                DeltaChoice(
+                    index=1, delta=ChoiceDelta(content="lo "), finish_reason=None
+                )
+            ],
+            created=100000,
+            model="model-id",
+            object="chat.completion.chunk",
+        ),
+        ChatCompletionChunk(
+            id="1",
+            choices=[
+                DeltaChoice(
+                    index=2, delta=ChoiceDelta(content="world"), finish_reason="stop"
+                )
+            ],
+            created=100000,
+            model="model-id",
+            object="chat.completion.chunk",
+        ),
+    ]
+
+    client.chat.completions._post = mock.Mock(return_value=returned_stream)
+    with start_transaction(name="openai tx"):
+        response_stream = client.chat.completions.create(
+            model="some-model",
+            messages=messages,
+        )
+        response_string = "".join(
+            map(lambda x: x.choices[0].delta.content, response_stream)
+        )
+    assert response_string == "hello world"
+    tx = events[0]
+    assert tx["type"] == "transaction"
+    span = tx["spans"][0]
+    assert span["op"] == "gen_ai.chat"
+
+    param_id = request.node.callspec.id
+    if "blocks" in param_id:
+        assert json.loads(span["data"][SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS]) == [
+            {
+                "type": "text",
+                "content": "You are a helpful assistant.",
+            }
+        ]
+    else:
+        assert json.loads(span["data"][SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS]) == [
+            {
+                "type": "text",
+                "content": "You are a helpful assistant.",
+            },
+            {
+                "type": "text",
+                "content": "Be concise and clear.",
+            },
+        ]
+
+    assert "hello" in span["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES]
+    assert "hello world" in span["data"][SPANDATA.GEN_AI_RESPONSE_TEXT]
+
+    try:
+        import tiktoken  # type: ignore # noqa # pylint: disable=unused-import
+
+        if "blocks" in param_id:
+            assert span["data"]["gen_ai.usage.output_tokens"] == 2
+            assert span["data"]["gen_ai.usage.input_tokens"] == 7
+            assert span["data"]["gen_ai.usage.total_tokens"] == 9
+        else:
+            assert span["data"]["gen_ai.usage.output_tokens"] == 2
+            assert span["data"]["gen_ai.usage.input_tokens"] == 1
+            assert span["data"]["gen_ai.usage.total_tokens"] == 3
     except ImportError:
         pass  # if tiktoken is not installed, we can't guarantee token usage will be calculated properly
 
@@ -315,9 +631,13 @@ def test_streaming_chat_completion(
 @pytest.mark.asyncio
 @pytest.mark.parametrize(
     "send_default_pii, include_prompts",
-    [(True, True), (True, False), (False, True), (False, False)],
+    [
+        (True, False),
+        (False, True),
+        (False, False),
+    ],
 )
-async def test_streaming_chat_completion_async(
+async def test_streaming_chat_completion_async_no_prompts(
     sentry_init, capture_events, send_default_pii, include_prompts
 ):
     sentry_init(
@@ -377,7 +697,11 @@ async def test_streaming_chat_completion_async(
     client.chat.completions._post = AsyncMock(return_value=returned_stream)
     with start_transaction(name="openai tx"):
         response_stream = await client.chat.completions.create(
-            model="some-model", messages=[{"role": "system", "content": "hello"}]
+            model="some-model",
+            messages=[
+                {"role": "system", "content": "You are a helpful assistant."},
+                {"role": "user", "content": "hello"},
+            ],
         )
 
         response_string = ""
@@ -390,19 +714,160 @@ async def test_streaming_chat_completion_async(
     span = tx["spans"][0]
     assert span["op"] == "gen_ai.chat"
 
-    if send_default_pii and include_prompts:
-        assert "hello" in span["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES]
-        assert "hello world" in span["data"][SPANDATA.GEN_AI_RESPONSE_TEXT]
-    else:
-        assert SPANDATA.GEN_AI_REQUEST_MESSAGES not in span["data"]
-        assert SPANDATA.GEN_AI_RESPONSE_TEXT not in span["data"]
+    assert SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS not in span["data"]
+    assert SPANDATA.GEN_AI_REQUEST_MESSAGES not in span["data"]
+    assert SPANDATA.GEN_AI_RESPONSE_TEXT not in span["data"]
 
     try:
         import tiktoken  # type: ignore # noqa # pylint: disable=unused-import
 
         assert span["data"]["gen_ai.usage.output_tokens"] == 2
-        assert span["data"]["gen_ai.usage.input_tokens"] == 1
-        assert span["data"]["gen_ai.usage.total_tokens"] == 3
+        assert span["data"]["gen_ai.usage.input_tokens"] == 7
+        assert span["data"]["gen_ai.usage.total_tokens"] == 9
+
+    except ImportError:
+        pass  # if tiktoken is not installed, we can't guarantee token usage will be calculated properly
+
+
+# noinspection PyTypeChecker
+@pytest.mark.asyncio
+@pytest.mark.parametrize(
+    "messages",
+    [
+        pytest.param(
+            [
+                {
+                    "role": "system",
+                    "content": "You are a helpful assistant.",
+                },
+                {"role": "user", "content": "hello"},
+            ],
+            id="blocks",
+        ),
+        pytest.param(
+            [
+                {
+                    "role": "system",
+                    "content": [
+                        {"type": "text", "text": "You are a helpful assistant."},
+                        {"type": "text", "text": "Be concise and clear."},
+                    ],
+                },
+                {"role": "user", "content": "hello"},
+            ],
+            id="parts",
+        ),
+    ],
+)
+async def test_streaming_chat_completion_async(
+    sentry_init, capture_events, messages, request
+):
+    sentry_init(
+        integrations=[
+            OpenAIIntegration(
+                include_prompts=True,
+                tiktoken_encoding_name=tiktoken_encoding_if_installed(),
+            )
+        ],
+        traces_sample_rate=1.0,
+        send_default_pii=True,
+    )
+    events = capture_events()
+
+    client = AsyncOpenAI(api_key="z")
+    returned_stream = AsyncStream(cast_to=None, response=None, client=client)
+    returned_stream._iterator = async_iterator(
+        [
+            ChatCompletionChunk(
+                id="1",
+                choices=[
+                    DeltaChoice(
+                        index=0, delta=ChoiceDelta(content="hel"), finish_reason=None
+                    )
+                ],
+                created=100000,
+                model="model-id",
+                object="chat.completion.chunk",
+            ),
+            ChatCompletionChunk(
+                id="1",
+                choices=[
+                    DeltaChoice(
+                        index=1, delta=ChoiceDelta(content="lo "), finish_reason=None
+                    )
+                ],
+                created=100000,
+                model="model-id",
+                object="chat.completion.chunk",
+            ),
+            ChatCompletionChunk(
+                id="1",
+                choices=[
+                    DeltaChoice(
+                        index=2,
+                        delta=ChoiceDelta(content="world"),
+                        finish_reason="stop",
+                    )
+                ],
+                created=100000,
+                model="model-id",
+                object="chat.completion.chunk",
+            ),
+        ]
+    )
+
+    client.chat.completions._post = AsyncMock(return_value=returned_stream)
+    with start_transaction(name="openai tx"):
+        response_stream = await client.chat.completions.create(
+            model="some-model",
+            messages=messages,
+        )
+
+        response_string = ""
+        async for x in response_stream:
+            response_string += x.choices[0].delta.content
+
+    assert response_string == "hello world"
+    tx = events[0]
+    assert tx["type"] == "transaction"
+    span = tx["spans"][0]
+    assert span["op"] == "gen_ai.chat"
+
+    param_id = request.node.callspec.id
+    if "blocks" in param_id:
+        assert json.loads(span["data"][SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS]) == [
+            {
+                "type": "text",
+                "content": "You are a helpful assistant.",
+            }
+        ]
+    else:
+        assert json.loads(span["data"][SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS]) == [
+            {
+                "type": "text",
+                "content": "You are a helpful assistant.",
+            },
+            {
+                "type": "text",
+                "content": "Be concise and clear.",
+            },
+        ]
+
+    assert "hello" in span["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES]
+    assert "hello world" in span["data"][SPANDATA.GEN_AI_RESPONSE_TEXT]
+
+    try:
+        import tiktoken  # type: ignore # noqa # pylint: disable=unused-import
+
+        if "blocks" in param_id:
+            assert span["data"]["gen_ai.usage.output_tokens"] == 2
+            assert span["data"]["gen_ai.usage.input_tokens"] == 7
+            assert span["data"]["gen_ai.usage.total_tokens"] == 9
+        else:
+            assert span["data"]["gen_ai.usage.output_tokens"] == 2
+            assert span["data"]["gen_ai.usage.input_tokens"] == 1
+            assert span["data"]["gen_ai.usage.total_tokens"] == 3
+
     except ImportError:
         pass  # if tiktoken is not installed, we can't guarantee token usage will be calculated properly
 
@@ -1034,12 +1499,79 @@ def test_ai_client_span_responses_api_no_pii(sentry_init, capture_events):
         "thread.name": mock.ANY,
     }
 
+    assert "gen_ai.system_instructions" not in spans[0]["data"]
     assert "gen_ai.request.messages" not in spans[0]["data"]
     assert "gen_ai.response.text" not in spans[0]["data"]
 
 
+@pytest.mark.parametrize(
+    "instructions",
+    (
+        omit,
+        None,
+        "You are a coding assistant that talks like a pirate.",
+    ),
+)
+@pytest.mark.parametrize(
+    "input",
+    [
+        pytest.param(
+            "How do I check if a Python object is an instance of a class?", id="string"
+        ),
+        pytest.param(
+            [
+                {
+                    "role": "system",
+                    "content": "You are a helpful assistant.",
+                },
+                {"role": "user", "content": "hello"},
+            ],
+            id="blocks_no_type",
+        ),
+        pytest.param(
+            [
+                {
+                    "type": "message",
+                    "role": "system",
+                    "content": "You are a helpful assistant.",
+                },
+                {"type": "message", "role": "user", "content": "hello"},
+            ],
+            id="blocks",
+        ),
+        pytest.param(
+            [
+                {
+                    "role": "system",
+                    "content": [
+                        {"type": "text", "text": "You are a helpful assistant."},
+                        {"type": "text", "text": "Be concise and clear."},
+                    ],
+                },
+                {"role": "user", "content": "hello"},
+            ],
+            id="parts_no_type",
+        ),
+        pytest.param(
+            [
+                {
+                    "type": "message",
+                    "role": "system",
+                    "content": [
+                        {"type": "text", "text": "You are a helpful assistant."},
+                        {"type": "text", "text": "Be concise and clear."},
+                    ],
+                },
+                {"type": "message", "role": "user", "content": "hello"},
+            ],
+            id="parts",
+        ),
+    ],
+)
 @pytest.mark.skipif(SKIP_RESPONSES_TESTS, reason="Responses API not available")
-def test_ai_client_span_responses_api(sentry_init, capture_events):
+def test_ai_client_span_responses_api(
+    sentry_init, capture_events, instructions, input, request
+):
     sentry_init(
         integrations=[OpenAIIntegration(include_prompts=True)],
         traces_sample_rate=1.0,
@@ -1053,8 +1585,8 @@ def test_ai_client_span_responses_api(sentry_init, capture_events):
     with start_transaction(name="openai tx"):
         client.responses.create(
             model="gpt-4o",
-            instructions="You are a coding assistant that talks like a pirate.",
-            input="How do I check if a Python object is an instance of a class?",
+            instructions=instructions,
+            input=input,
         )
 
     (transaction,) = events
@@ -1063,10 +1595,9 @@ def test_ai_client_span_responses_api(sentry_init, capture_events):
     assert len(spans) == 1
     assert spans[0]["op"] == "gen_ai.responses"
     assert spans[0]["origin"] == "auto.ai.openai"
-    assert spans[0]["data"] == {
+
+    expected_data = {
         "gen_ai.operation.name": "responses",
-        "gen_ai.request.messages": '["How do I check if a Python object is an instance of a class?"]',
-        "gen_ai.request.model": "gpt-4o",
         "gen_ai.system": "openai",
         "gen_ai.response.model": "response-model-id",
         "gen_ai.usage.input_tokens": 20,
@@ -1074,11 +1605,169 @@ def test_ai_client_span_responses_api(sentry_init, capture_events):
         "gen_ai.usage.output_tokens": 10,
         "gen_ai.usage.output_tokens.reasoning": 8,
         "gen_ai.usage.total_tokens": 30,
+        "gen_ai.request.model": "gpt-4o",
         "gen_ai.response.text": "the model response",
+        "sentry.sdk_meta.gen_ai.input.messages.original_length": 1,
         "thread.id": mock.ANY,
         "thread.name": mock.ANY,
     }
 
+    param_id = request.node.callspec.id
+    if "string" in param_id and (
+        instructions is None or isinstance(instructions, Omit)
+    ):  # type: ignore
+        expected_data.update(
+            {
+                "gen_ai.request.messages": safe_serialize(
+                    ["How do I check if a Python object is an instance of a class?"]
+                ),
+            }
+        )
+    elif "string" in param_id:
+        expected_data.update(
+            {
+                "gen_ai.system_instructions": safe_serialize(
+                    [
+                        {
+                            "type": "text",
+                            "content": "You are a coding assistant that talks like a pirate.",
+                        }
+                    ]
+                ),
+                "gen_ai.request.messages": safe_serialize(
+                    ["How do I check if a Python object is an instance of a class?"]
+                ),
+            }
+        )
+    elif "blocks_no_type" in param_id and (
+        instructions is None or isinstance(instructions, Omit)
+    ):  # type: ignore
+        expected_data.update(
+            {
+                "gen_ai.system_instructions": safe_serialize(
+                    [{"type": "text", "content": "You are a helpful assistant."}]
+                ),
+                "gen_ai.request.messages": safe_serialize(
+                    [{"role": "user", "content": "hello"}]
+                ),
+            }
+        )
+    elif "blocks_no_type" in param_id:
+        expected_data.update(
+            {
+                "gen_ai.system_instructions": safe_serialize(
+                    [
+                        {
+                            "type": "text",
+                            "content": "You are a coding assistant that talks like a pirate.",
+                        },
+                        {"type": "text", "content": "You are a helpful assistant."},
+                    ]
+                ),
+                "gen_ai.request.messages": safe_serialize(
+                    [{"role": "user", "content": "hello"}]
+                ),
+            }
+        )
+    elif "blocks" in param_id and (
+        instructions is None or isinstance(instructions, Omit)
+    ):  # type: ignore
+        expected_data.update(
+            {
+                "gen_ai.system_instructions": safe_serialize(
+                    [{"type": "text", "content": "You are a helpful assistant."}]
+                ),
+                "gen_ai.request.messages": safe_serialize(
+                    [{"type": "message", "role": "user", "content": "hello"}]
+                ),
+            }
+        )
+    elif "blocks" in param_id:
+        expected_data.update(
+            {
+                "gen_ai.system_instructions": safe_serialize(
+                    [
+                        {
+                            "type": "text",
+                            "content": "You are a coding assistant that talks like a pirate.",
+                        },
+                        {"type": "text", "content": "You are a helpful assistant."},
+                    ]
+                ),
+                "gen_ai.request.messages": safe_serialize(
+                    [{"type": "message", "role": "user", "content": "hello"}]
+                ),
+            }
+        )
+    elif "parts_no_type" in param_id and (
+        instructions is None or isinstance(instructions, Omit)
+    ):  # type: ignore
+        expected_data.update(
+            {
+                "gen_ai.system_instructions": safe_serialize(
+                    [
+                        {"type": "text", "content": "You are a helpful assistant."},
+                        {"type": "text", "content": "Be concise and clear."},
+                    ]
+                ),
+                "gen_ai.request.messages": safe_serialize(
+                    [{"role": "user", "content": "hello"}]
+                ),
+            }
+        )
+    elif "parts_no_type" in param_id:
+        expected_data.update(
+            {
+                "gen_ai.system_instructions": safe_serialize(
+                    [
+                        {
+                            "type": "text",
+                            "content": "You are a coding assistant that talks like a pirate.",
+                        },
+                        {"type": "text", "content": "You are a helpful assistant."},
+                        {"type": "text", "content": "Be concise and clear."},
+                    ]
+                ),
+                "gen_ai.request.messages": safe_serialize(
+                    [{"role": "user", "content": "hello"}]
+                ),
+            }
+        )
+    elif instructions is None or isinstance(instructions, Omit):  # type: ignore
+        expected_data.update(
+            {
+                "gen_ai.system_instructions": safe_serialize(
+                    [
+                        {"type": "text", "content": "You are a helpful assistant."},
+                        {"type": "text", "content": "Be concise and clear."},
+                    ]
+                ),
+                "gen_ai.request.messages": safe_serialize(
+                    [{"type": "message", "role": "user", "content": "hello"}]
+                ),
+            }
+        )
+    else:
+        expected_data.update(
+            {
+                "gen_ai.system_instructions": safe_serialize(
+                    [
+                        {
+                            "type": "text",
+                            "content": "You are a coding assistant that talks like a pirate.",
+                        },
+                        {"type": "text", "content": "You are a helpful assistant."},
+                        {"type": "text", "content": "Be concise and clear."},
+                    ]
+                ),
+                "gen_ai.request.messages": safe_serialize(
+                    [{"type": "message", "role": "user", "content": "hello"}]
+                ),
+            }
+        )
+
+    assert spans[0]["data"] == expected_data
+
 
 @pytest.mark.skipif(SKIP_RESPONSES_TESTS, reason="Responses API not available")
 def test_error_in_responses_api(sentry_init, capture_events):
@@ -1119,7 +1808,73 @@ def test_error_in_responses_api(sentry_init, capture_events):
 
 @pytest.mark.asyncio
 @pytest.mark.skipif(SKIP_RESPONSES_TESTS, reason="Responses API not available")
-async def test_ai_client_span_responses_async_api(sentry_init, capture_events):
+@pytest.mark.parametrize(
+    "instructions",
+    (
+        omit,
+        None,
+        "You are a coding assistant that talks like a pirate.",
+    ),
+)
+@pytest.mark.parametrize(
+    "input",
+    [
+        pytest.param(
+            "How do I check if a Python object is an instance of a class?", id="string"
+        ),
+        pytest.param(
+            [
+                {
+                    "role": "system",
+                    "content": "You are a helpful assistant.",
+                },
+                {"role": "user", "content": "hello"},
+            ],
+            id="blocks_no_type",
+        ),
+        pytest.param(
+            [
+                {
+                    "type": "message",
+                    "role": "system",
+                    "content": "You are a helpful assistant.",
+                },
+                {"type": "message", "role": "user", "content": "hello"},
+            ],
+            id="blocks",
+        ),
+        pytest.param(
+            [
+                {
+                    "role": "system",
+                    "content": [
+                        {"type": "text", "text": "You are a helpful assistant."},
+                        {"type": "text", "text": "Be concise and clear."},
+                    ],
+                },
+                {"role": "user", "content": "hello"},
+            ],
+            id="parts_no_type",
+        ),
+        pytest.param(
+            [
+                {
+                    "type": "message",
+                    "role": "system",
+                    "content": [
+                        {"type": "text", "text": "You are a helpful assistant."},
+                        {"type": "text", "text": "Be concise and clear."},
+                    ],
+                },
+                {"type": "message", "role": "user", "content": "hello"},
+            ],
+            id="parts",
+        ),
+    ],
+)
+async def test_ai_client_span_responses_async_api(
+    sentry_init, capture_events, instructions, input, request
+):
     sentry_init(
         integrations=[OpenAIIntegration(include_prompts=True)],
         traces_sample_rate=1.0,
@@ -1133,8 +1888,8 @@ async def test_ai_client_span_responses_async_api(sentry_init, capture_events):
     with start_transaction(name="openai tx"):
         await client.responses.create(
             model="gpt-4o",
-            instructions="You are a coding assistant that talks like a pirate.",
-            input="How do I check if a Python object is an instance of a class?",
+            instructions=instructions,
+            input=input,
         )
 
     (transaction,) = events
@@ -1143,7 +1898,8 @@ async def test_ai_client_span_responses_async_api(sentry_init, capture_events):
     assert len(spans) == 1
     assert spans[0]["op"] == "gen_ai.responses"
     assert spans[0]["origin"] == "auto.ai.openai"
-    assert spans[0]["data"] == {
+
+    expected_data = {
         "gen_ai.operation.name": "responses",
         "gen_ai.request.messages": '["How do I check if a Python object is an instance of a class?"]',
         "gen_ai.request.model": "gpt-4o",
@@ -1155,15 +1911,236 @@ async def test_ai_client_span_responses_async_api(sentry_init, capture_events):
         "gen_ai.usage.output_tokens.reasoning": 8,
         "gen_ai.usage.total_tokens": 30,
         "gen_ai.response.text": "the model response",
+        "sentry.sdk_meta.gen_ai.input.messages.original_length": 1,
         "thread.id": mock.ANY,
         "thread.name": mock.ANY,
     }
 
+    param_id = request.node.callspec.id
+    if "string" in param_id and (
+        instructions is None or isinstance(instructions, Omit)
+    ):  # type: ignore
+        expected_data.update(
+            {
+                "gen_ai.request.messages": safe_serialize(
+                    ["How do I check if a Python object is an instance of a class?"]
+                ),
+            }
+        )
+    elif "string" in param_id:
+        expected_data.update(
+            {
+                "gen_ai.system_instructions": safe_serialize(
+                    [
+                        {
+                            "type": "text",
+                            "content": "You are a coding assistant that talks like a pirate.",
+                        }
+                    ]
+                ),
+                "gen_ai.request.messages": safe_serialize(
+                    ["How do I check if a Python object is an instance of a class?"]
+                ),
+            }
+        )
+    elif "blocks_no_type" in param_id and (
+        instructions is None or isinstance(instructions, Omit)
+    ):  # type: ignore
+        expected_data.update(
+            {
+                "gen_ai.system_instructions": safe_serialize(
+                    [{"type": "text", "content": "You are a helpful assistant."}]
+                ),
+                "gen_ai.request.messages": safe_serialize(
+                    [{"role": "user", "content": "hello"}]
+                ),
+            }
+        )
+    elif "blocks_no_type" in param_id:
+        expected_data.update(
+            {
+                "gen_ai.system_instructions": safe_serialize(
+                    [
+                        {
+                            "type": "text",
+                            "content": "You are a coding assistant that talks like a pirate.",
+                        },
+                        {"type": "text", "content": "You are a helpful assistant."},
+                    ]
+                ),
+                "gen_ai.request.messages": safe_serialize(
+                    [{"role": "user", "content": "hello"}]
+                ),
+            }
+        )
+    elif "blocks" in param_id and (
+        instructions is None or isinstance(instructions, Omit)
+    ):  # type: ignore
+        expected_data.update(
+            {
+                "gen_ai.system_instructions": safe_serialize(
+                    [{"type": "text", "content": "You are a helpful assistant."}]
+                ),
+                "gen_ai.request.messages": safe_serialize(
+                    [{"type": "message", "role": "user", "content": "hello"}]
+                ),
+            }
+        )
+    elif "blocks" in param_id:
+        expected_data.update(
+            {
+                "gen_ai.system_instructions": safe_serialize(
+                    [
+                        {
+                            "type": "text",
+                            "content": "You are a coding assistant that talks like a pirate.",
+                        },
+                        {"type": "text", "content": "You are a helpful assistant."},
+                    ]
+                ),
+                "gen_ai.request.messages": safe_serialize(
+                    [{"type": "message", "role": "user", "content": "hello"}]
+                ),
+            }
+        )
+    elif "parts_no_type" in param_id and (
+        instructions is None or isinstance(instructions, Omit)
+    ):  # type: ignore
+        expected_data.update(
+            {
+                "gen_ai.system_instructions": safe_serialize(
+                    [
+                        {"type": "text", "content": "You are a helpful assistant."},
+                        {"type": "text", "content": "Be concise and clear."},
+                    ]
+                ),
+                "gen_ai.request.messages": safe_serialize(
+                    [{"role": "user", "content": "hello"}]
+                ),
+            }
+        )
+    elif "parts_no_type" in param_id:
+        expected_data.update(
+            {
+                "gen_ai.system_instructions": safe_serialize(
+                    [
+                        {
+                            "type": "text",
+                            "content": "You are a coding assistant that talks like a pirate.",
+                        },
+                        {"type": "text", "content": "You are a helpful assistant."},
+                        {"type": "text", "content": "Be concise and clear."},
+                    ]
+                ),
+                "gen_ai.request.messages": safe_serialize(
+                    [{"role": "user", "content": "hello"}]
+                ),
+            }
+        )
+    elif instructions is None or isinstance(instructions, Omit):  # type: ignore
+        expected_data.update(
+            {
+                "gen_ai.system_instructions": safe_serialize(
+                    [
+                        {"type": "text", "content": "You are a helpful assistant."},
+                        {"type": "text", "content": "Be concise and clear."},
+                    ]
+                ),
+                "gen_ai.request.messages": safe_serialize(
+                    [{"type": "message", "role": "user", "content": "hello"}]
+                ),
+            }
+        )
+    else:
+        expected_data.update(
+            {
+                "gen_ai.system_instructions": safe_serialize(
+                    [
+                        {
+                            "type": "text",
+                            "content": "You are a coding assistant that talks like a pirate.",
+                        },
+                        {"type": "text", "content": "You are a helpful assistant."},
+                        {"type": "text", "content": "Be concise and clear."},
+                    ]
+                ),
+                "gen_ai.request.messages": safe_serialize(
+                    [{"type": "message", "role": "user", "content": "hello"}]
+                ),
+            }
+        )
+
+    assert spans[0]["data"] == expected_data
+
 
 @pytest.mark.asyncio
+@pytest.mark.parametrize(
+    "instructions",
+    (
+        omit,
+        None,
+        "You are a coding assistant that talks like a pirate.",
+    ),
+)
+@pytest.mark.parametrize(
+    "input",
+    [
+        pytest.param(
+            "How do I check if a Python object is an instance of a class?", id="string"
+        ),
+        pytest.param(
+            [
+                {
+                    "role": "system",
+                    "content": "You are a helpful assistant.",
+                },
+                {"role": "user", "content": "hello"},
+            ],
+            id="blocks_no_type",
+        ),
+        pytest.param(
+            [
+                {
+                    "type": "message",
+                    "role": "system",
+                    "content": "You are a helpful assistant.",
+                },
+                {"type": "message", "role": "user", "content": "hello"},
+            ],
+            id="blocks",
+        ),
+        pytest.param(
+            [
+                {
+                    "role": "system",
+                    "content": [
+                        {"type": "text", "text": "You are a helpful assistant."},
+                        {"type": "text", "text": "Be concise and clear."},
+                    ],
+                },
+                {"role": "user", "content": "hello"},
+            ],
+            id="parts_no_type",
+        ),
+        pytest.param(
+            [
+                {
+                    "type": "message",
+                    "role": "system",
+                    "content": [
+                        {"type": "text", "text": "You are a helpful assistant."},
+                        {"type": "text", "text": "Be concise and clear."},
+                    ],
+                },
+                {"type": "message", "role": "user", "content": "hello"},
+            ],
+            id="parts",
+        ),
+    ],
+)
 @pytest.mark.skipif(SKIP_RESPONSES_TESTS, reason="Responses API not available")
 async def test_ai_client_span_streaming_responses_async_api(
-    sentry_init, capture_events
+    sentry_init, capture_events, instructions, input, request
 ):
     sentry_init(
         integrations=[OpenAIIntegration(include_prompts=True)],
@@ -1178,8 +2155,8 @@ async def test_ai_client_span_streaming_responses_async_api(
     with start_transaction(name="openai tx"):
         await client.responses.create(
             model="gpt-4o",
-            instructions="You are a coding assistant that talks like a pirate.",
-            input="How do I check if a Python object is an instance of a class?",
+            instructions=instructions,
+            input=input,
             stream=True,
         )
 
@@ -1189,23 +2166,180 @@ async def test_ai_client_span_streaming_responses_async_api(
     assert len(spans) == 1
     assert spans[0]["op"] == "gen_ai.responses"
     assert spans[0]["origin"] == "auto.ai.openai"
-    assert spans[0]["data"] == {
+
+    expected_data = {
         "gen_ai.operation.name": "responses",
-        "gen_ai.request.messages": '["How do I check if a Python object is an instance of a class?"]',
-        "gen_ai.request.model": "gpt-4o",
-        "gen_ai.response.model": "response-model-id",
         "gen_ai.response.streaming": True,
         "gen_ai.system": "openai",
+        "gen_ai.response.model": "response-model-id",
         "gen_ai.usage.input_tokens": 20,
         "gen_ai.usage.input_tokens.cached": 5,
         "gen_ai.usage.output_tokens": 10,
         "gen_ai.usage.output_tokens.reasoning": 8,
         "gen_ai.usage.total_tokens": 30,
+        "gen_ai.request.model": "gpt-4o",
         "gen_ai.response.text": "the model response",
+        "sentry.sdk_meta.gen_ai.input.messages.original_length": 1,
         "thread.id": mock.ANY,
         "thread.name": mock.ANY,
     }
 
+    param_id = request.node.callspec.id
+    if "string" in param_id and (
+        instructions is None or isinstance(instructions, Omit)
+    ):  # type: ignore
+        expected_data.update(
+            {
+                "gen_ai.request.messages": safe_serialize(
+                    ["How do I check if a Python object is an instance of a class?"]
+                ),
+            }
+        )
+    elif "string" in param_id:
+        expected_data.update(
+            {
+                "gen_ai.system_instructions": safe_serialize(
+                    [
+                        {
+                            "type": "text",
+                            "content": "You are a coding assistant that talks like a pirate.",
+                        }
+                    ]
+                ),
+                "gen_ai.request.messages": safe_serialize(
+                    ["How do I check if a Python object is an instance of a class?"]
+                ),
+            }
+        )
+    elif "blocks_no_type" in param_id and (
+        instructions is None or isinstance(instructions, Omit)
+    ):  # type: ignore
+        expected_data.update(
+            {
+                "gen_ai.system_instructions": safe_serialize(
+                    [{"type": "text", "content": "You are a helpful assistant."}]
+                ),
+                "gen_ai.request.messages": safe_serialize(
+                    [{"role": "user", "content": "hello"}]
+                ),
+            }
+        )
+    elif "blocks_no_type" in param_id:
+        expected_data.update(
+            {
+                "gen_ai.system_instructions": safe_serialize(
+                    [
+                        {
+                            "type": "text",
+                            "content": "You are a coding assistant that talks like a pirate.",
+                        },
+                        {"type": "text", "content": "You are a helpful assistant."},
+                    ]
+                ),
+                "gen_ai.request.messages": safe_serialize(
+                    [{"role": "user", "content": "hello"}]
+                ),
+            }
+        )
+    elif "blocks" in param_id and (
+        instructions is None or isinstance(instructions, Omit)
+    ):  # type: ignore
+        expected_data.update(
+            {
+                "gen_ai.system_instructions": safe_serialize(
+                    [{"type": "text", "content": "You are a helpful assistant."}]
+                ),
+                "gen_ai.request.messages": safe_serialize(
+                    [{"type": "message", "role": "user", "content": "hello"}]
+                ),
+            }
+        )
+    elif "blocks" in param_id:
+        expected_data.update(
+            {
+                "gen_ai.system_instructions": safe_serialize(
+                    [
+                        {
+                            "type": "text",
+                            "content": "You are a coding assistant that talks like a pirate.",
+                        },
+                        {"type": "text", "content": "You are a helpful assistant."},
+                    ]
+                ),
+                "gen_ai.request.messages": safe_serialize(
+                    [{"type": "message", "role": "user", "content": "hello"}]
+                ),
+            }
+        )
+    elif "parts_no_type" in param_id and (
+        instructions is None or isinstance(instructions, Omit)
+    ):  # type: ignore
+        expected_data.update(
+            {
+                "gen_ai.system_instructions": safe_serialize(
+                    [
+                        {"type": "text", "content": "You are a helpful assistant."},
+                        {"type": "text", "content": "Be concise and clear."},
+                    ]
+                ),
+                "gen_ai.request.messages": safe_serialize(
+                    [{"role": "user", "content": "hello"}]
+                ),
+            }
+        )
+    elif "parts_no_type" in param_id:
+        expected_data.update(
+            {
+                "gen_ai.system_instructions": safe_serialize(
+                    [
+                        {
+                            "type": "text",
+                            "content": "You are a coding assistant that talks like a pirate.",
+                        },
+                        {"type": "text", "content": "You are a helpful assistant."},
+                        {"type": "text", "content": "Be concise and clear."},
+                    ]
+                ),
+                "gen_ai.request.messages": safe_serialize(
+                    [{"role": "user", "content": "hello"}]
+                ),
+            }
+        )
+    elif instructions is None or isinstance(instructions, Omit):  # type: ignore
+        expected_data.update(
+            {
+                "gen_ai.system_instructions": safe_serialize(
+                    [
+                        {"type": "text", "content": "You are a helpful assistant."},
+                        {"type": "text", "content": "Be concise and clear."},
+                    ]
+                ),
+                "gen_ai.request.messages": safe_serialize(
+                    [{"type": "message", "role": "user", "content": "hello"}]
+                ),
+            }
+        )
+    else:
+        expected_data.update(
+            {
+                "gen_ai.system_instructions": safe_serialize(
+                    [
+                        {
+                            "type": "text",
+                            "content": "You are a coding assistant that talks like a pirate.",
+                        },
+                        {"type": "text", "content": "You are a helpful assistant."},
+                        {"type": "text", "content": "Be concise and clear."},
+                    ]
+                ),
+                "gen_ai.request.messages": safe_serialize(
+                    [{"type": "message", "role": "user", "content": "hello"}]
+                ),
+            }
+        )
+
+    assert spans[0]["data"] == expected_data
+
 
 @pytest.mark.asyncio
 @pytest.mark.skipif(SKIP_RESPONSES_TESTS, reason="Responses API not available")
@@ -1458,7 +2592,24 @@ def test_empty_tools_in_chat_completion(sentry_init, capture_events, tools):
     assert "gen_ai.request.available_tools" not in span["data"]
 
 
-def test_openai_message_role_mapping(sentry_init, capture_events):
+# Test messages with mixed roles including "ai" that should be mapped to "assistant"
+@pytest.mark.parametrize(
+    "test_message,expected_role",
+    [
+        ({"role": "user", "content": "Hello"}, "user"),
+        (
+            {"role": "ai", "content": "Hi there!"},
+            "assistant",
+        ),  # Should be mapped to "assistant"
+        (
+            {"role": "assistant", "content": "How can I help?"},
+            "assistant",
+        ),  # Should stay "assistant"
+    ],
+)
+def test_openai_message_role_mapping(
+    sentry_init, capture_events, test_message, expected_role
+):
     """Test that OpenAI integration properly maps message roles like 'ai' to 'assistant'"""
 
     sentry_init(
@@ -1470,13 +2621,8 @@ def test_openai_message_role_mapping(sentry_init, capture_events):
 
     client = OpenAI(api_key="z")
     client.chat.completions._post = mock.Mock(return_value=EXAMPLE_CHAT_COMPLETION)
-    # Test messages with mixed roles including "ai" that should be mapped to "assistant"
-    test_messages = [
-        {"role": "system", "content": "You are helpful."},
-        {"role": "user", "content": "Hello"},
-        {"role": "ai", "content": "Hi there!"},  # Should be mapped to "assistant"
-        {"role": "assistant", "content": "How can I help?"},  # Should stay "assistant"
-    ]
+
+    test_messages = [test_message]
 
     with start_transaction(name="openai tx"):
         client.chat.completions.create(model="test-model", messages=test_messages)
@@ -1491,22 +2637,8 @@ def test_openai_message_role_mapping(sentry_init, capture_events):
 
     stored_messages = json.loads(span["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES])
 
-    # Verify that "ai" role was mapped to "assistant"
-    assert len(stored_messages) == 4
-    assert stored_messages[0]["role"] == "system"
-    assert stored_messages[1]["role"] == "user"
-    assert (
-        stored_messages[2]["role"] == "assistant"
-    )  # "ai" should be mapped to "assistant"
-    assert stored_messages[3]["role"] == "assistant"  # should stay "assistant"
-
-    # Verify content is preserved
-    assert stored_messages[2]["content"] == "Hi there!"
-    assert stored_messages[3]["content"] == "How can I help?"
-
-    # Verify no "ai" roles remain
-    roles = [msg["role"] for msg in stored_messages]
-    assert "ai" not in roles
+    assert len(stored_messages) == 1
+    assert stored_messages[0]["role"] == expected_role
 
 
 def test_openai_message_truncation(sentry_init, capture_events):
@@ -1548,14 +2680,207 @@ def test_openai_message_truncation(sentry_init, capture_events):
     assert isinstance(parsed_messages, list)
     assert len(parsed_messages) <= len(large_messages)
 
-    if "_meta" in event and len(parsed_messages) < len(large_messages):
-        meta_path = event["_meta"]
-        if (
-            "spans" in meta_path
-            and "0" in meta_path["spans"]
-            and "data" in meta_path["spans"]["0"]
-        ):
-            span_meta = meta_path["spans"]["0"]["data"]
-            if SPANDATA.GEN_AI_REQUEST_MESSAGES in span_meta:
-                messages_meta = span_meta[SPANDATA.GEN_AI_REQUEST_MESSAGES]
-                assert "len" in messages_meta.get("", {})
+    meta_path = event["_meta"]
+    span_meta = meta_path["spans"]["0"]["data"]
+    messages_meta = span_meta[SPANDATA.GEN_AI_REQUEST_MESSAGES]
+    assert "len" in messages_meta.get("", {})
+
+
+# noinspection PyTypeChecker
+def test_streaming_chat_completion_ttft(sentry_init, capture_events):
+    """
+    Test that streaming chat completions capture time-to-first-token (TTFT).
+    """
+    sentry_init(
+        integrations=[OpenAIIntegration()],
+        traces_sample_rate=1.0,
+    )
+    events = capture_events()
+
+    client = OpenAI(api_key="z")
+    returned_stream = Stream(cast_to=None, response=None, client=client)
+    returned_stream._iterator = [
+        ChatCompletionChunk(
+            id="1",
+            choices=[
+                DeltaChoice(
+                    index=0, delta=ChoiceDelta(content="Hello"), finish_reason=None
+                )
+            ],
+            created=100000,
+            model="model-id",
+            object="chat.completion.chunk",
+        ),
+        ChatCompletionChunk(
+            id="1",
+            choices=[
+                DeltaChoice(
+                    index=0, delta=ChoiceDelta(content=" world"), finish_reason="stop"
+                )
+            ],
+            created=100000,
+            model="model-id",
+            object="chat.completion.chunk",
+        ),
+    ]
+
+    client.chat.completions._post = mock.Mock(return_value=returned_stream)
+
+    with start_transaction(name="openai tx"):
+        response_stream = client.chat.completions.create(
+            model="some-model", messages=[{"role": "user", "content": "Say hello"}]
+        )
+        # Consume the stream
+        for _ in response_stream:
+            pass
+
+    (tx,) = events
+    span = tx["spans"][0]
+    assert span["op"] == "gen_ai.chat"
+
+    # Verify TTFT is captured
+    assert SPANDATA.GEN_AI_RESPONSE_TIME_TO_FIRST_TOKEN in span["data"]
+    ttft = span["data"][SPANDATA.GEN_AI_RESPONSE_TIME_TO_FIRST_TOKEN]
+    assert isinstance(ttft, float)
+    assert ttft > 0
+
+
+# noinspection PyTypeChecker
+@pytest.mark.asyncio
+async def test_streaming_chat_completion_ttft_async(sentry_init, capture_events):
+    """
+    Test that async streaming chat completions capture time-to-first-token (TTFT).
+    """
+    sentry_init(
+        integrations=[OpenAIIntegration()],
+        traces_sample_rate=1.0,
+    )
+    events = capture_events()
+
+    client = AsyncOpenAI(api_key="z")
+    returned_stream = AsyncStream(cast_to=None, response=None, client=client)
+    returned_stream._iterator = async_iterator(
+        [
+            ChatCompletionChunk(
+                id="1",
+                choices=[
+                    DeltaChoice(
+                        index=0, delta=ChoiceDelta(content="Hello"), finish_reason=None
+                    )
+                ],
+                created=100000,
+                model="model-id",
+                object="chat.completion.chunk",
+            ),
+            ChatCompletionChunk(
+                id="1",
+                choices=[
+                    DeltaChoice(
+                        index=0,
+                        delta=ChoiceDelta(content=" world"),
+                        finish_reason="stop",
+                    )
+                ],
+                created=100000,
+                model="model-id",
+                object="chat.completion.chunk",
+            ),
+        ]
+    )
+
+    client.chat.completions._post = AsyncMock(return_value=returned_stream)
+
+    with start_transaction(name="openai tx"):
+        response_stream = await client.chat.completions.create(
+            model="some-model", messages=[{"role": "user", "content": "Say hello"}]
+        )
+        # Consume the stream
+        async for _ in response_stream:
+            pass
+
+    (tx,) = events
+    span = tx["spans"][0]
+    assert span["op"] == "gen_ai.chat"
+
+    # Verify TTFT is captured
+    assert SPANDATA.GEN_AI_RESPONSE_TIME_TO_FIRST_TOKEN in span["data"]
+    ttft = span["data"][SPANDATA.GEN_AI_RESPONSE_TIME_TO_FIRST_TOKEN]
+    assert isinstance(ttft, float)
+    assert ttft > 0
+
+
+# noinspection PyTypeChecker
+@pytest.mark.skipif(SKIP_RESPONSES_TESTS, reason="Responses API not available")
+def test_streaming_responses_api_ttft(sentry_init, capture_events):
+    """
+    Test that streaming responses API captures time-to-first-token (TTFT).
+    """
+    sentry_init(
+        integrations=[OpenAIIntegration()],
+        traces_sample_rate=1.0,
+    )
+    events = capture_events()
+
+    client = OpenAI(api_key="z")
+    returned_stream = Stream(cast_to=None, response=None, client=client)
+    returned_stream._iterator = EXAMPLE_RESPONSES_STREAM
+    client.responses._post = mock.Mock(return_value=returned_stream)
+
+    with start_transaction(name="openai tx"):
+        response_stream = client.responses.create(
+            model="some-model",
+            input="hello",
+            stream=True,
+        )
+        # Consume the stream
+        for _ in response_stream:
+            pass
+
+    (tx,) = events
+    span = tx["spans"][0]
+    assert span["op"] == "gen_ai.responses"
+
+    # Verify TTFT is captured
+    assert SPANDATA.GEN_AI_RESPONSE_TIME_TO_FIRST_TOKEN in span["data"]
+    ttft = span["data"][SPANDATA.GEN_AI_RESPONSE_TIME_TO_FIRST_TOKEN]
+    assert isinstance(ttft, float)
+    assert ttft > 0
+
+
+# noinspection PyTypeChecker
+@pytest.mark.asyncio
+@pytest.mark.skipif(SKIP_RESPONSES_TESTS, reason="Responses API not available")
+async def test_streaming_responses_api_ttft_async(sentry_init, capture_events):
+    """
+    Test that async streaming responses API captures time-to-first-token (TTFT).
+    """
+    sentry_init(
+        integrations=[OpenAIIntegration()],
+        traces_sample_rate=1.0,
+    )
+    events = capture_events()
+
+    client = AsyncOpenAI(api_key="z")
+    returned_stream = AsyncStream(cast_to=None, response=None, client=client)
+    returned_stream._iterator = async_iterator(EXAMPLE_RESPONSES_STREAM)
+    client.responses._post = AsyncMock(return_value=returned_stream)
+
+    with start_transaction(name="openai tx"):
+        response_stream = await client.responses.create(
+            model="some-model",
+            input="hello",
+            stream=True,
+        )
+        # Consume the stream
+        async for _ in response_stream:
+            pass
+
+    (tx,) = events
+    span = tx["spans"][0]
+    assert span["op"] == "gen_ai.responses"
+
+    # Verify TTFT is captured
+    assert SPANDATA.GEN_AI_RESPONSE_TIME_TO_FIRST_TOKEN in span["data"]
+    ttft = span["data"][SPANDATA.GEN_AI_RESPONSE_TIME_TO_FIRST_TOKEN]
+    assert isinstance(ttft, float)
+    assert ttft > 0
diff --git a/tests/integrations/openai_agents/test_openai_agents.py b/tests/integrations/openai_agents/test_openai_agents.py
index c5cb25dfee..4bf212b8f3 100644
--- a/tests/integrations/openai_agents/test_openai_agents.py
+++ b/tests/integrations/openai_agents/test_openai_agents.py
@@ -12,6 +12,12 @@
 from sentry_sdk.integrations.openai_agents.utils import _set_input_data, safe_serialize
 from sentry_sdk.utils import parse_version
 
+from openai import AsyncOpenAI
+from agents.models.openai_responses import OpenAIResponsesModel
+
+from unittest import mock
+from unittest.mock import AsyncMock
+
 import agents
 from agents import (
     Agent,
@@ -25,9 +31,11 @@
     ResponseOutputText,
     ResponseFunctionToolCall,
 )
+from agents.tool import HostedMCPTool
 from agents.exceptions import MaxTurnsExceeded, ModelBehaviorError
 from agents.version import __version__ as OPENAI_AGENTS_VERSION
 
+from openai.types.responses import Response, ResponseUsage
 from openai.types.responses.response_usage import (
     InputTokensDetails,
     OutputTokensDetails,
@@ -35,6 +43,42 @@
 
 test_run_config = agents.RunConfig(tracing_disabled=True)
 
+EXAMPLE_RESPONSE = Response(
+    id="chat-id",
+    output=[
+        ResponseOutputMessage(
+            id="message-id",
+            content=[
+                ResponseOutputText(
+                    annotations=[],
+                    text="the model response",
+                    type="output_text",
+                ),
+            ],
+            role="assistant",
+            status="completed",
+            type="message",
+        ),
+    ],
+    parallel_tool_calls=False,
+    tool_choice="none",
+    tools=[],
+    created_at=10000000,
+    model="response-model-id",
+    object="response",
+    usage=ResponseUsage(
+        input_tokens=20,
+        input_tokens_details=InputTokensDetails(
+            cached_tokens=5,
+        ),
+        output_tokens=10,
+        output_tokens_details=OutputTokensDetails(
+            reasoning_tokens=8,
+        ),
+        total_tokens=30,
+    ),
+)
+
 
 @pytest.fixture
 def mock_usage():
@@ -88,6 +132,26 @@ def test_agent():
     )
 
 
+@pytest.fixture
+def test_agent_with_instructions():
+    def inner(instructions):
+        """Create a real Agent instance for testing."""
+        return Agent(
+            name="test_agent",
+            instructions=instructions,
+            model="gpt-4",
+            model_settings=ModelSettings(
+                max_tokens=100,
+                temperature=0.7,
+                top_p=1.0,
+                presence_penalty=0.0,
+                frequency_penalty=0.0,
+            ),
+        )
+
+    return inner
+
+
 @pytest.fixture
 def test_agent_custom_model():
     """Create a real Agent instance for testing."""
@@ -107,8 +171,145 @@ def test_agent_custom_model():
 
 
 @pytest.mark.asyncio
-async def test_agent_invocation_span(
+async def test_agent_invocation_span_no_pii(
     sentry_init, capture_events, test_agent, mock_model_response
+):
+    with patch.dict(os.environ, {"OPENAI_API_KEY": "test-key"}):
+        with patch(
+            "agents.models.openai_responses.OpenAIResponsesModel.get_response"
+        ) as mock_get_response:
+            mock_get_response.return_value = mock_model_response
+
+            sentry_init(
+                integrations=[OpenAIAgentsIntegration()],
+                traces_sample_rate=1.0,
+                send_default_pii=False,
+            )
+
+            events = capture_events()
+
+            result = await agents.Runner.run(
+                test_agent, "Test input", run_config=test_run_config
+            )
+
+            assert result is not None
+            assert result.final_output == "Hello, how can I help you?"
+
+    (transaction,) = events
+    spans = transaction["spans"]
+    invoke_agent_span, ai_client_span = spans
+
+    assert transaction["transaction"] == "test_agent workflow"
+    assert transaction["contexts"]["trace"]["origin"] == "auto.ai.openai_agents"
+
+    assert invoke_agent_span["description"] == "invoke_agent test_agent"
+
+    assert SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS not in invoke_agent_span["data"]
+    assert "gen_ai.request.messages" not in invoke_agent_span["data"]
+    assert "gen_ai.response.text" not in invoke_agent_span["data"]
+
+    assert invoke_agent_span["data"]["gen_ai.operation.name"] == "invoke_agent"
+    assert invoke_agent_span["data"]["gen_ai.system"] == "openai"
+    assert invoke_agent_span["data"]["gen_ai.agent.name"] == "test_agent"
+    assert invoke_agent_span["data"]["gen_ai.request.max_tokens"] == 100
+    assert invoke_agent_span["data"]["gen_ai.request.model"] == "gpt-4"
+    assert invoke_agent_span["data"]["gen_ai.request.temperature"] == 0.7
+    assert invoke_agent_span["data"]["gen_ai.request.top_p"] == 1.0
+
+    assert ai_client_span["description"] == "chat gpt-4"
+    assert ai_client_span["data"]["gen_ai.operation.name"] == "chat"
+    assert ai_client_span["data"]["gen_ai.system"] == "openai"
+    assert ai_client_span["data"]["gen_ai.agent.name"] == "test_agent"
+    assert ai_client_span["data"]["gen_ai.request.max_tokens"] == 100
+    assert ai_client_span["data"]["gen_ai.request.model"] == "gpt-4"
+    assert ai_client_span["data"]["gen_ai.request.temperature"] == 0.7
+    assert ai_client_span["data"]["gen_ai.request.top_p"] == 1.0
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize(
+    "instructions",
+    (
+        None,
+        "You are a coding assistant that talks like a pirate.",
+    ),
+)
+@pytest.mark.parametrize(
+    "input",
+    [
+        pytest.param("Test input", id="string"),
+        pytest.param(
+            [
+                {
+                    "role": "system",
+                    "content": "You are a helpful assistant.",
+                },
+                {
+                    "role": "user",
+                    "content": "Test input",
+                },
+            ],
+            id="blocks_no_type",
+        ),
+        pytest.param(
+            [
+                {
+                    "type": "message",
+                    "role": "system",
+                    "content": "You are a helpful assistant.",
+                },
+                {
+                    "type": "message",
+                    "role": "user",
+                    "content": "Test input",
+                },
+            ],
+            id="blocks",
+        ),
+        pytest.param(
+            [
+                {
+                    "role": "system",
+                    "content": [
+                        {"type": "text", "text": "You are a helpful assistant."},
+                        {"type": "text", "text": "Be concise and clear."},
+                    ],
+                },
+                {
+                    "role": "user",
+                    "content": "Test input",
+                },
+            ],
+            id="parts_no_type",
+        ),
+        pytest.param(
+            [
+                {
+                    "type": "message",
+                    "role": "system",
+                    "content": [
+                        {"type": "text", "text": "You are a helpful assistant."},
+                        {"type": "text", "text": "Be concise and clear."},
+                    ],
+                },
+                {
+                    "type": "message",
+                    "role": "user",
+                    "content": "Test input",
+                },
+            ],
+            id="parts",
+        ),
+    ],
+)
+async def test_agent_invocation_span(
+    sentry_init,
+    capture_events,
+    test_agent_with_instructions,
+    mock_model_response,
+    instructions,
+    input,
+    request,
 ):
     """
     Test that the integration creates spans for agent invocations.
@@ -129,7 +330,9 @@ async def test_agent_invocation_span(
             events = capture_events()
 
             result = await agents.Runner.run(
-                test_agent, "Test input", run_config=test_run_config
+                test_agent_with_instructions(instructions),
+                input,
+                run_config=test_run_config,
             )
 
             assert result is not None
@@ -143,21 +346,101 @@ async def test_agent_invocation_span(
     assert transaction["contexts"]["trace"]["origin"] == "auto.ai.openai_agents"
 
     assert invoke_agent_span["description"] == "invoke_agent test_agent"
-    assert invoke_agent_span["data"]["gen_ai.request.messages"] == safe_serialize(
-        [
-            {
-                "content": [
-                    {"text": "You are a helpful test assistant.", "type": "text"}
-                ],
-                "role": "system",
-            },
-            {"content": [{"text": "Test input", "type": "text"}], "role": "user"},
-        ]
-    )
+
+    # Only first case checks "gen_ai.request.messages" until further input handling work.
+    param_id = request.node.callspec.id
+    if "string" in param_id and instructions is None:  # type: ignore
+        assert "gen_ai.system_instructions" not in ai_client_span["data"]
+
+        assert invoke_agent_span["data"]["gen_ai.request.messages"] == safe_serialize(
+            [
+                {"content": [{"text": "Test input", "type": "text"}], "role": "user"},
+            ]
+        )
+
+    elif "string" in param_id:
+        assert ai_client_span["data"]["gen_ai.system_instructions"] == safe_serialize(
+            [
+                {
+                    "type": "text",
+                    "content": "You are a coding assistant that talks like a pirate.",
+                },
+            ]
+        )
+    elif "blocks_no_type" in param_id and instructions is None:  # type: ignore
+        assert ai_client_span["data"]["gen_ai.system_instructions"] == safe_serialize(
+            [
+                {"type": "text", "content": "You are a helpful assistant."},
+            ]
+        )
+    elif "blocks_no_type" in param_id:
+        assert ai_client_span["data"]["gen_ai.system_instructions"] == safe_serialize(
+            [
+                {
+                    "type": "text",
+                    "content": "You are a coding assistant that talks like a pirate.",
+                },
+                {"type": "text", "content": "You are a helpful assistant."},
+            ]
+        )
+    elif "blocks" in param_id and instructions is None:  # type: ignore
+        assert ai_client_span["data"]["gen_ai.system_instructions"] == safe_serialize(
+            [
+                {"type": "text", "content": "You are a helpful assistant."},
+            ]
+        )
+    elif "blocks" in param_id:
+        assert ai_client_span["data"]["gen_ai.system_instructions"] == safe_serialize(
+            [
+                {
+                    "type": "text",
+                    "content": "You are a coding assistant that talks like a pirate.",
+                },
+                {"type": "text", "content": "You are a helpful assistant."},
+            ]
+        )
+    elif "parts_no_type" in param_id and instructions is None:
+        assert ai_client_span["data"]["gen_ai.system_instructions"] == safe_serialize(
+            [
+                {"type": "text", "content": "You are a helpful assistant."},
+                {"type": "text", "content": "Be concise and clear."},
+            ]
+        )
+    elif "parts_no_type" in param_id:
+        assert ai_client_span["data"]["gen_ai.system_instructions"] == safe_serialize(
+            [
+                {
+                    "type": "text",
+                    "content": "You are a coding assistant that talks like a pirate.",
+                },
+                {"type": "text", "content": "You are a helpful assistant."},
+                {"type": "text", "content": "Be concise and clear."},
+            ]
+        )
+    elif instructions is None:  # type: ignore
+        assert ai_client_span["data"]["gen_ai.system_instructions"] == safe_serialize(
+            [
+                {"type": "text", "content": "You are a helpful assistant."},
+                {"type": "text", "content": "Be concise and clear."},
+            ]
+        )
+    else:
+        assert ai_client_span["data"]["gen_ai.system_instructions"] == safe_serialize(
+            [
+                {
+                    "type": "text",
+                    "content": "You are a coding assistant that talks like a pirate.",
+                },
+                {"type": "text", "content": "You are a helpful assistant."},
+                {"type": "text", "content": "Be concise and clear."},
+            ]
+        )
+
     assert (
         invoke_agent_span["data"]["gen_ai.response.text"]
         == "Hello, how can I help you?"
     )
+
     assert invoke_agent_span["data"]["gen_ai.operation.name"] == "invoke_agent"
     assert invoke_agent_span["data"]["gen_ai.system"] == "openai"
     assert invoke_agent_span["data"]["gen_ai.agent.name"] == "test_agent"
@@ -212,8 +495,11 @@ async def test_client_span_custom_model(
     assert ai_client_span["data"]["gen_ai.request.model"] == "my-custom-model"
 
 
-def test_agent_invocation_span_sync(
-    sentry_init, capture_events, test_agent, mock_model_response
+def test_agent_invocation_span_sync_no_pii(
+    sentry_init,
+    capture_events,
+    test_agent,
+    mock_model_response,
 ):
     """
     Test that the integration creates spans for agent invocations.
@@ -228,6 +514,7 @@ def test_agent_invocation_span_sync(
             sentry_init(
                 integrations=[OpenAIAgentsIntegration()],
                 traces_sample_rate=1.0,
+                send_default_pii=False,
             )
 
             events = capture_events()
@@ -264,6 +551,226 @@ def test_agent_invocation_span_sync(
     assert ai_client_span["data"]["gen_ai.request.temperature"] == 0.7
     assert ai_client_span["data"]["gen_ai.request.top_p"] == 1.0
 
+    assert SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS not in invoke_agent_span["data"]
+
+
+@pytest.mark.parametrize(
+    "instructions",
+    (
+        None,
+        "You are a coding assistant that talks like a pirate.",
+    ),
+)
+@pytest.mark.parametrize(
+    "input",
+    [
+        pytest.param("Test input", id="string"),
+        pytest.param(
+            [
+                {
+                    "role": "system",
+                    "content": "You are a helpful assistant.",
+                },
+                {
+                    "role": "user",
+                    "content": "Test input",
+                },
+            ],
+            id="blocks_no_type",
+        ),
+        pytest.param(
+            [
+                {
+                    "type": "message",
+                    "role": "system",
+                    "content": "You are a helpful assistant.",
+                },
+                {
+                    "type": "message",
+                    "role": "user",
+                    "content": "Test input",
+                },
+            ],
+            id="blocks",
+        ),
+        pytest.param(
+            [
+                {
+                    "role": "system",
+                    "content": [
+                        {"type": "text", "text": "You are a helpful assistant."},
+                        {"type": "text", "text": "Be concise and clear."},
+                    ],
+                },
+                {
+                    "role": "user",
+                    "content": "Test input",
+                },
+            ],
+            id="parts_no_type",
+        ),
+        pytest.param(
+            [
+                {
+                    "type": "message",
+                    "role": "system",
+                    "content": [
+                        {"type": "text", "text": "You are a helpful assistant."},
+                        {"type": "text", "text": "Be concise and clear."},
+                    ],
+                },
+                {
+                    "type": "message",
+                    "role": "user",
+                    "content": "Test input",
+                },
+            ],
+            id="parts",
+        ),
+    ],
+)
+def test_agent_invocation_span_sync(
+    sentry_init,
+    capture_events,
+    test_agent_with_instructions,
+    mock_model_response,
+    instructions,
+    input,
+    request,
+):
+    """
+    Test that the integration creates spans for agent invocations.
+    """
+
+    with patch.dict(os.environ, {"OPENAI_API_KEY": "test-key"}):
+        with patch(
+            "agents.models.openai_responses.OpenAIResponsesModel.get_response"
+        ) as mock_get_response:
+            mock_get_response.return_value = mock_model_response
+
+            sentry_init(
+                integrations=[OpenAIAgentsIntegration()],
+                traces_sample_rate=1.0,
+                send_default_pii=True,
+            )
+
+            events = capture_events()
+
+            result = agents.Runner.run_sync(
+                test_agent_with_instructions(instructions),
+                input,
+                run_config=test_run_config,
+            )
+
+            assert result is not None
+            assert result.final_output == "Hello, how can I help you?"
+
+    (transaction,) = events
+    spans = transaction["spans"]
+    invoke_agent_span, ai_client_span = spans
+
+    assert transaction["transaction"] == "test_agent workflow"
+    assert transaction["contexts"]["trace"]["origin"] == "auto.ai.openai_agents"
+
+    assert invoke_agent_span["description"] == "invoke_agent test_agent"
+    assert invoke_agent_span["data"]["gen_ai.operation.name"] == "invoke_agent"
+    assert invoke_agent_span["data"]["gen_ai.system"] == "openai"
+    assert invoke_agent_span["data"]["gen_ai.agent.name"] == "test_agent"
+    assert invoke_agent_span["data"]["gen_ai.request.max_tokens"] == 100
+    assert invoke_agent_span["data"]["gen_ai.request.model"] == "gpt-4"
+    assert invoke_agent_span["data"]["gen_ai.request.temperature"] == 0.7
+    assert invoke_agent_span["data"]["gen_ai.request.top_p"] == 1.0
+
+    assert ai_client_span["description"] == "chat gpt-4"
+    assert ai_client_span["data"]["gen_ai.operation.name"] == "chat"
+    assert ai_client_span["data"]["gen_ai.system"] == "openai"
+    assert ai_client_span["data"]["gen_ai.agent.name"] == "test_agent"
+    assert ai_client_span["data"]["gen_ai.request.max_tokens"] == 100
+    assert ai_client_span["data"]["gen_ai.request.model"] == "gpt-4"
+    assert ai_client_span["data"]["gen_ai.request.temperature"] == 0.7
+    assert ai_client_span["data"]["gen_ai.request.top_p"] == 1.0
+
+    param_id = request.node.callspec.id
+    if "string" in param_id and instructions is None:  # type: ignore
+        assert "gen_ai.system_instructions" not in ai_client_span["data"]
+    elif "string" in param_id:
+        assert ai_client_span["data"]["gen_ai.system_instructions"] == safe_serialize(
+            [
+                {
+                    "type": "text",
+                    "content": "You are a coding assistant that talks like a pirate.",
+                },
+            ]
+        )
+    elif "blocks_no_type" in param_id and instructions is None:  # type: ignore
+        assert ai_client_span["data"]["gen_ai.system_instructions"] == safe_serialize(
+            [
+                {"type": "text", "content": "You are a helpful assistant."},
+            ]
+        )
+    elif "blocks_no_type" in param_id:
+        assert ai_client_span["data"]["gen_ai.system_instructions"] == safe_serialize(
+            [
+                {
+                    "type": "text",
+                    "content": "You are a coding assistant that talks like a pirate.",
+                },
+                {"type": "text", "content": "You are a helpful assistant."},
+            ]
+        )
+    elif "blocks" in param_id and instructions is None:  # type: ignore
+        assert ai_client_span["data"]["gen_ai.system_instructions"] == safe_serialize(
+            [
+                {"type": "text", "content": "You are a helpful assistant."},
+            ]
+        )
+    elif "blocks" in param_id:
+        assert ai_client_span["data"]["gen_ai.system_instructions"] == safe_serialize(
+            [
+                {
+                    "type": "text",
+                    "content": "You are a coding assistant that talks like a pirate.",
+                },
+                {"type": "text", "content": "You are a helpful assistant."},
+            ]
+        )
+    elif "parts_no_type" in param_id and instructions is None:
+        assert ai_client_span["data"]["gen_ai.system_instructions"] == safe_serialize(
+            [
+                {"type": "text", "content": "You are a helpful assistant."},
+                {"type": "text", "content": "Be concise and clear."},
+            ]
+        )
+    elif "parts_no_type" in param_id:
+        assert ai_client_span["data"]["gen_ai.system_instructions"] == safe_serialize(
+            [
+                {
+                    "type": "text",
+                    "content": "You are a coding assistant that talks like a pirate.",
+                },
+                {"type": "text", "content": "You are a helpful assistant."},
+                {"type": "text", "content": "Be concise and clear."},
+            ]
+        )
+    elif instructions is None:  # type: ignore
+        assert ai_client_span["data"]["gen_ai.system_instructions"] == safe_serialize(
+            [
+                {"type": "text", "content": "You are a helpful assistant."},
+                {"type": "text", "content": "Be concise and clear."},
+            ]
+        )
+    else:
+        assert ai_client_span["data"]["gen_ai.system_instructions"] == safe_serialize(
+            [
+                {
+                    "type": "text",
+                    "content": "You are a coding assistant that talks like a pirate.",
+                },
+                {"type": "text", "content": "You are a helpful assistant."},
+                {"type": "text", "content": "Be concise and clear."},
+            ]
+        )
+
 
 @pytest.mark.asyncio
 async def test_handoff_span(sentry_init, capture_events, mock_usage):
@@ -573,12 +1080,6 @@ def simple_test_tool(message: str) -> str:
     assert ai_client_span1["data"]["gen_ai.request.max_tokens"] == 100
     assert ai_client_span1["data"]["gen_ai.request.messages"] == safe_serialize(
         [
-            {
-                "role": "system",
-                "content": [
-                    {"type": "text", "text": "You are a helpful test assistant."}
-                ],
-            },
             {
                 "role": "user",
                 "content": [
@@ -644,30 +1145,6 @@ def simple_test_tool(message: str) -> str:
     assert ai_client_span2["data"]["gen_ai.request.max_tokens"] == 100
     assert ai_client_span2["data"]["gen_ai.request.messages"] == safe_serialize(
         [
-            {
-                "role": "system",
-                "content": [
-                    {"type": "text", "text": "You are a helpful test assistant."}
-                ],
-            },
-            {
-                "role": "user",
-                "content": [
-                    {"type": "text", "text": "Please use the simple test tool"}
-                ],
-            },
-            {
-                "role": "assistant",
-                "content": [
-                    {
-                        "arguments": '{"message": "hello"}',
-                        "call_id": "call_123",
-                        "name": "simple_test_tool",
-                        "type": "function_call",
-                        "id": "call_123",
-                    }
-                ],
-            },
             {
                 "role": "tool",
                 "content": [
@@ -695,6 +1172,87 @@ def simple_test_tool(message: str) -> str:
     assert ai_client_span2["data"]["gen_ai.usage.total_tokens"] == 25
 
 
+@pytest.mark.asyncio
+async def test_hosted_mcp_tool_propagation_headers(sentry_init, test_agent):
+    """
+    Test responses API is given trace propagation headers with HostedMCPTool.
+    """
+
+    hosted_tool = HostedMCPTool(
+        tool_config={
+            "type": "mcp",
+            "server_label": "test_server",
+            "server_url": "http://example.com/",
+            "headers": {
+                "baggage": "custom=data",
+            },
+        },
+    )
+
+    client = AsyncOpenAI(api_key="z")
+    client.responses._post = AsyncMock(return_value=EXAMPLE_RESPONSE)
+
+    model = OpenAIResponsesModel(model="gpt-4", openai_client=client)
+
+    agent_with_tool = test_agent.clone(
+        tools=[hosted_tool],
+        model=model,
+    )
+
+    sentry_init(
+        integrations=[OpenAIAgentsIntegration()],
+        traces_sample_rate=1.0,
+        release="d08ebdb9309e1b004c6f52202de58a09c2268e42",
+    )
+
+    with patch.object(
+        model._client.responses,
+        "create",
+        wraps=model._client.responses.create,
+    ) as create, mock.patch(
+        "sentry_sdk.tracing_utils.Random.randrange", return_value=500000
+    ):
+        with sentry_sdk.start_transaction(
+            name="/interactions/other-dogs/new-dog",
+            op="greeting.sniff",
+            trace_id="01234567890123456789012345678901",
+        ) as transaction:
+            await agents.Runner.run(
+                agent_with_tool,
+                "Please use the simple test tool",
+                run_config=test_run_config,
+            )
+
+            ai_client_span = transaction._span_recorder.spans[-1]
+
+        args, kwargs = create.call_args
+
+        assert "tools" in kwargs
+        assert len(kwargs["tools"]) == 1
+        hosted_mcp_tool = kwargs["tools"][0]
+
+        assert hosted_mcp_tool["headers"][
+            "sentry-trace"
+        ] == "{trace_id}-{parent_span_id}-{sampled}".format(
+            trace_id=transaction.trace_id,
+            parent_span_id=ai_client_span.span_id,
+            sampled=1,
+        )
+
+        expected_outgoing_baggage = (
+            "custom=data,"
+            "sentry-trace_id=01234567890123456789012345678901,"
+            "sentry-sample_rand=0.500000,"
+            "sentry-environment=production,"
+            "sentry-release=d08ebdb9309e1b004c6f52202de58a09c2268e42,"
+            "sentry-transaction=/interactions/other-dogs/new-dog,"
+            "sentry-sample_rate=1.0,"
+            "sentry-sampled=true"
+        )
+
+        assert hosted_mcp_tool["headers"]["baggage"] == expected_outgoing_baggage
+
+
 @pytest.mark.asyncio
 async def test_model_behavior_error(sentry_init, capture_events, test_agent):
     """
@@ -857,12 +1415,6 @@ async def test_error_captures_input_data(sentry_init, capture_events, test_agent
     assert "gen_ai.request.messages" in ai_client_span["data"]
     request_messages = safe_serialize(
         [
-            {
-                "role": "system",
-                "content": [
-                    {"type": "text", "text": "You are a helpful test assistant."}
-                ],
-            },
             {"role": "user", "content": [{"type": "text", "text": "Test input"}]},
         ]
     )
@@ -1241,7 +1793,24 @@ async def run():
     assert txn3["transaction"] == "test_agent workflow"
 
 
-def test_openai_agents_message_role_mapping(sentry_init, capture_events):
+# Test input messages with mixed roles including "ai"
+@pytest.mark.parametrize(
+    "test_message,expected_role",
+    [
+        ({"role": "user", "content": "Hello"}, "user"),
+        (
+            {"role": "ai", "content": "Hi there!"},
+            "assistant",
+        ),  # Should be mapped to "assistant"
+        (
+            {"role": "assistant", "content": "How can I help?"},
+            "assistant",
+        ),  # Should stay "assistant"
+    ],
+)
+def test_openai_agents_message_role_mapping(
+    sentry_init, capture_events, test_message, expected_role
+):
     """Test that OpenAI Agents integration properly maps message roles like 'ai' to 'assistant'"""
     sentry_init(
         integrations=[OpenAIAgentsIntegration()],
@@ -1249,15 +1818,7 @@ def test_openai_agents_message_role_mapping(sentry_init, capture_events):
         send_default_pii=True,
     )
 
-    # Test input messages with mixed roles including "ai"
-    test_input = [
-        {"role": "system", "content": "You are helpful."},
-        {"role": "user", "content": "Hello"},
-        {"role": "ai", "content": "Hi there!"},  # Should be mapped to "assistant"
-        {"role": "assistant", "content": "How can I help?"},  # Should stay "assistant"
-    ]
-
-    get_response_kwargs = {"input": test_input}
+    get_response_kwargs = {"input": [test_message]}
 
     from sentry_sdk.integrations.openai_agents.utils import _set_input_data
     from sentry_sdk import start_span
@@ -1268,23 +1829,10 @@ def test_openai_agents_message_role_mapping(sentry_init, capture_events):
     # Verify that messages were processed and roles were mapped
     from sentry_sdk.consts import SPANDATA
 
-    if SPANDATA.GEN_AI_REQUEST_MESSAGES in span._data:
-        import json
-
-        stored_messages = json.loads(span._data[SPANDATA.GEN_AI_REQUEST_MESSAGES])
-
-        # Verify roles were properly mapped
-        found_assistant_roles = 0
-        for message in stored_messages:
-            if message["role"] == "assistant":
-                found_assistant_roles += 1
-
-        # Should have 2 assistant roles (1 from original "assistant", 1 from mapped "ai")
-        assert found_assistant_roles == 2
+    stored_messages = json.loads(span._data[SPANDATA.GEN_AI_REQUEST_MESSAGES])
 
-        # Verify no "ai" roles remain in any message
-        for message in stored_messages:
-            assert message["role"] != "ai"
+    # Verify roles were properly mapped
+    assert stored_messages[0]["role"] == expected_role
 
 
 @pytest.mark.asyncio
@@ -1465,7 +2013,7 @@ async def test_ai_client_span_includes_response_model(
 ):
     """
     Test that ai_client spans (gen_ai.chat) include the response model from the actual API response.
-    This verifies the new functionality to capture the model used in the response.
+    This verifies we capture the actual model used (which may differ from the requested model).
     """
 
     with patch.dict(os.environ, {"OPENAI_API_KEY": "test-key"}):
@@ -1473,7 +2021,7 @@ async def test_ai_client_span_includes_response_model(
         with patch(
             "agents.models.openai_responses.OpenAIResponsesModel._fetch_response"
         ) as mock_fetch_response:
-            # Create a mock OpenAI Response object with a model field
+            # Create a mock OpenAI Response object with a specific model version
             mock_response = MagicMock()
             mock_response.model = "gpt-4.1-2025-04-14"  # The actual response model
             mock_response.id = "resp_123"
@@ -1523,7 +2071,7 @@ async def test_ai_client_span_includes_response_model(
     spans = transaction["spans"]
     _, ai_client_span = spans
 
-    # Verify ai_client span has response model
+    # Verify ai_client span has response model from API response
     assert ai_client_span["description"] == "chat gpt-4"
     assert "gen_ai.response.model" in ai_client_span["data"]
     assert ai_client_span["data"]["gen_ai.response.model"] == "gpt-4.1-2025-04-14"
@@ -1545,13 +2093,13 @@ async def test_ai_client_span_response_model_with_chat_completions(
     )
 
     with patch.dict(os.environ, {"OPENAI_API_KEY": "test-key"}):
-        # Mock the get_response method directly since ChatCompletions may use Responses API anyway
+        # Mock the _fetch_response method
         with patch(
             "agents.models.openai_responses.OpenAIResponsesModel._fetch_response"
         ) as mock_fetch_response:
-            # Create a mock Response object with a model field
+            # Create a mock Response object
             mock_response = MagicMock()
-            mock_response.model = "gpt-4o-mini-2024-07-18"  # Actual response model
+            mock_response.model = "gpt-4o-mini-2024-07-18"
             mock_response.id = "resp_123"
             mock_response.output = [
                 ResponseOutputMessage(
@@ -1598,7 +2146,7 @@ async def test_ai_client_span_response_model_with_chat_completions(
     spans = transaction["spans"]
     _, ai_client_span = spans
 
-    # Verify response model from Response is captured
+    # Verify response model from API response is captured
     assert "gen_ai.response.model" in ai_client_span["data"]
     assert ai_client_span["data"]["gen_ai.response.model"] == "gpt-4o-mini-2024-07-18"
 
@@ -1711,41 +2259,45 @@ async def test_response_model_not_set_when_unavailable(
     sentry_init, capture_events, test_agent
 ):
     """
-    Test that response model is not set if the raw response doesn't have a model field.
-    This can happen with custom model implementations.
+    Test that response model is not set if the API response doesn't have a model field.
+    The request model should still be set correctly.
     """
 
     with patch.dict(os.environ, {"OPENAI_API_KEY": "test-key"}):
-        # Mock without _fetch_response (simulating custom model without this method)
         with patch(
-            "agents.models.openai_responses.OpenAIResponsesModel.get_response"
-        ) as mock_get_response:
-            response = ModelResponse(
-                output=[
-                    ResponseOutputMessage(
-                        id="msg_123",
-                        type="message",
-                        status="completed",
-                        content=[
-                            ResponseOutputText(
-                                text="Response without model field",
-                                type="output_text",
-                                annotations=[],
-                            )
-                        ],
-                        role="assistant",
-                    )
-                ],
-                usage=Usage(
-                    requests=1,
-                    input_tokens=10,
-                    output_tokens=20,
-                    total_tokens=30,
-                ),
-                response_id="resp_123",
+            "agents.models.openai_responses.OpenAIResponsesModel._fetch_response"
+        ) as mock_fetch_response:
+            # Create a mock response without a model field
+            mock_response = MagicMock()
+            mock_response.model = None  # No model in response
+            mock_response.id = "resp_123"
+            mock_response.output = [
+                ResponseOutputMessage(
+                    id="msg_123",
+                    type="message",
+                    status="completed",
+                    content=[
+                        ResponseOutputText(
+                            text="Response without model field",
+                            type="output_text",
+                            annotations=[],
+                        )
+                    ],
+                    role="assistant",
+                )
+            ]
+            mock_response.usage = MagicMock()
+            mock_response.usage.input_tokens = 10
+            mock_response.usage.output_tokens = 20
+            mock_response.usage.total_tokens = 30
+            mock_response.usage.input_tokens_details = InputTokensDetails(
+                cached_tokens=0
+            )
+            mock_response.usage.output_tokens_details = OutputTokensDetails(
+                reasoning_tokens=0
             )
-            # Don't set _sentry_response_model attribute
-            mock_get_response.return_value = response
+
+            mock_fetch_response.return_value = mock_response
 
             sentry_init(
                 integrations=[OpenAIAgentsIntegration()],
@@ -1754,25 +2306,21 @@ async def test_response_model_not_set_when_unavailable(
 
             events = capture_events()
 
-            # Remove the _fetch_response method to simulate custom model
-            with patch.object(
-                agents.models.openai_responses.OpenAIResponsesModel,
-                "_fetch_response",
-                None,
-            ):
-                result = await agents.Runner.run(
-                    test_agent, "Test input", run_config=test_run_config
-                )
+            result = await agents.Runner.run(
+                test_agent, "Test input", run_config=test_run_config
+            )
 
-                assert result is not None
+            assert result is not None
 
     (transaction,) = events
     spans = transaction["spans"]
     _, ai_client_span = spans
 
-    # When response model can't be captured, it shouldn't be in the span data
-    # (we only set it when we can accurately capture it)
+    # Response model should NOT be set when API doesn't return it
     assert "gen_ai.response.model" not in ai_client_span["data"]
+    # But request model should still be set
+    assert "gen_ai.request.model" in ai_client_span["data"]
+    assert ai_client_span["data"]["gen_ai.request.model"] == "gpt-4"
 
 
 @pytest.mark.asyncio
@@ -1780,15 +2328,14 @@ async def test_invoke_agent_span_includes_response_model(
     sentry_init, capture_events, test_agent
 ):
     """
-    Test that invoke_agent spans include the response model.
-    When an agent makes multiple LLM calls, it should report the last model used.
+    Test that invoke_agent spans include the response model from the API response.
     """
 
     with patch.dict(os.environ, {"OPENAI_API_KEY": "test-key"}):
         with patch(
             "agents.models.openai_responses.OpenAIResponsesModel._fetch_response"
         ) as mock_fetch_response:
-            # Create a mock OpenAI Response object with a model field
+            # Create a mock OpenAI Response object with a specific model version
             mock_response = MagicMock()
             mock_response.model = "gpt-4.1-2025-04-14"  # The actual response model
             mock_response.id = "resp_123"
@@ -1838,7 +2385,7 @@ async def test_invoke_agent_span_includes_response_model(
     spans = transaction["spans"]
     invoke_agent_span, ai_client_span = spans
 
-    # Verify invoke_agent span has response model
+    # Verify invoke_agent span has response model from API
     assert invoke_agent_span["description"] == "invoke_agent test_agent"
     assert "gen_ai.response.model" in invoke_agent_span["data"]
     assert invoke_agent_span["data"]["gen_ai.response.model"] == "gpt-4.1-2025-04-14"
@@ -1868,7 +2415,7 @@ def calculator(a: int, b: int) -> int:
         with patch(
             "agents.models.openai_responses.OpenAIResponsesModel._fetch_response"
         ) as mock_fetch_response:
-            # First call: gpt-4 model
+            # First call: gpt-4 model returns tool call
             first_response = MagicMock()
             first_response.model = "gpt-4-0613"
             first_response.id = "resp_1"
@@ -1892,9 +2439,9 @@ def calculator(a: int, b: int) -> int:
                 reasoning_tokens=0
             )
 
-            # Second call: different model (e.g., after tool execution)
+            # Second call: different model version returns final message
             second_response = MagicMock()
-            second_response.model = "gpt-4.1-2025-04-14"  # Different model
+            second_response.model = "gpt-4.1-2025-04-14"
             second_response.id = "resp_2"
             second_response.output = [
                 ResponseOutputMessage(
@@ -1946,11 +2493,11 @@ def calculator(a: int, b: int) -> int:
     first_ai_client_span = spans[1]
     second_ai_client_span = spans[3]  # After tool span
 
-    # Verify invoke_agent span uses the LAST response model
+    # Invoke_agent span uses the LAST response model
     assert "gen_ai.response.model" in invoke_agent_span["data"]
     assert invoke_agent_span["data"]["gen_ai.response.model"] == "gpt-4.1-2025-04-14"
 
-    # Verify each ai_client span has its own response model
+    # Each ai_client span has its own response model from the API
     assert first_ai_client_span["data"]["gen_ai.response.model"] == "gpt-4-0613"
     assert (
         second_ai_client_span["data"]["gen_ai.response.model"] == "gpt-4.1-2025-04-14"
@@ -1971,7 +2518,6 @@ def test_openai_agents_message_truncation(sentry_init, capture_events):
     )
 
     test_messages = [
-        {"role": "system", "content": "small message 1"},
         {"role": "user", "content": large_content},
         {"role": "assistant", "content": large_content},
         {"role": "user", "content": "small message 4"},
@@ -1985,8 +2531,8 @@ def test_openai_agents_message_truncation(sentry_init, capture_events):
         _set_input_data(span, get_response_kwargs)
         if hasattr(scope, "_gen_ai_original_message_count"):
             truncated_count = scope._gen_ai_original_message_count.get(span.span_id)
-            assert truncated_count == 5, (
-                f"Expected 5 original messages, got {truncated_count}"
+            assert truncated_count == 4, (
+                f"Expected 4 original messages, got {truncated_count}"
             )
 
         assert SPANDATA.GEN_AI_REQUEST_MESSAGES in span._data
@@ -1995,6 +2541,172 @@ def test_openai_agents_message_truncation(sentry_init, capture_events):
 
         parsed_messages = json.loads(messages_data)
         assert isinstance(parsed_messages, list)
-        assert len(parsed_messages) == 2
-        assert "small message 4" in str(parsed_messages[0])
-        assert "small message 5" in str(parsed_messages[1])
+        assert len(parsed_messages) == 1
+        assert "small message 5" in str(parsed_messages[0])
+
+
+def test_streaming_patches_applied(sentry_init):
+    """
+    Test that the streaming patches are applied correctly.
+    """
+    sentry_init(
+        integrations=[OpenAIAgentsIntegration()],
+        traces_sample_rate=1.0,
+    )
+
+    # Verify that run_streamed is patched (will have __wrapped__ attribute if patched)
+    import agents
+
+    # Check that the method exists and has been modified
+    assert hasattr(agents.run.DEFAULT_AGENT_RUNNER, "run_streamed")
+    assert hasattr(agents.run.AgentRunner, "_run_single_turn_streamed")
+
+    # Verify the patches were applied by checking for our wrapper
+    run_streamed_func = agents.run.DEFAULT_AGENT_RUNNER.run_streamed
+    assert run_streamed_func is not None
+
+
+@pytest.mark.asyncio
+async def test_streaming_span_update_captures_response_data(
+    sentry_init, test_agent, mock_usage
+):
+    """
+    Test that update_ai_client_span correctly captures response text,
+    usage data, and response model from a streaming response.
+    """
+    from sentry_sdk.integrations.openai_agents.spans.ai_client import (
+        update_ai_client_span,
+    )
+
+    sentry_init(
+        integrations=[OpenAIAgentsIntegration()],
+        traces_sample_rate=1.0,
+        send_default_pii=True,
+    )
+
+    # Create a mock streaming response object (similar to what we'd get from ResponseCompletedEvent)
+    mock_streaming_response = MagicMock()
+    mock_streaming_response.model = "gpt-4-streaming"
+    mock_streaming_response.usage = mock_usage
+    mock_streaming_response.output = [
+        ResponseOutputMessage(
+            id="msg_streaming_123",
+            type="message",
+            status="completed",
+            content=[
+                ResponseOutputText(
+                    text="Hello from streaming!",
+                    type="output_text",
+                    annotations=[],
+                )
+            ],
+            role="assistant",
+        )
+    ]
+
+    # Test the unified update function (works for both streaming and non-streaming)
+    with start_span(op="gen_ai.chat", description="test chat") as span:
+        update_ai_client_span(span, mock_streaming_response)
+
+        # Verify the span data was set correctly
+        assert span._data["gen_ai.response.text"] == "Hello from streaming!"
+        assert span._data["gen_ai.usage.input_tokens"] == 10
+        assert span._data["gen_ai.usage.output_tokens"] == 20
+        assert span._data["gen_ai.response.model"] == "gpt-4-streaming"
+
+
+@pytest.mark.asyncio
+async def test_streaming_ttft_on_chat_span(sentry_init, test_agent):
+    """
+    Test that time-to-first-token (TTFT) is recorded on chat spans during streaming.
+
+    TTFT is triggered by events with a `delta` attribute, which includes:
+    - ResponseTextDeltaEvent (text output)
+    - ResponseAudioDeltaEvent (audio output)
+    - ResponseReasoningTextDeltaEvent (reasoning/thinking)
+    - ResponseFunctionCallArgumentsDeltaEvent (function call args)
+    - and other delta events...
+
+    Events WITHOUT delta (like ResponseCompletedEvent, ResponseCreatedEvent, etc.)
+    should NOT trigger TTFT.
+    """
+    from sentry_sdk.integrations.openai_agents.patches.models import (
+        _create_get_model_wrapper,
+    )
+
+    sentry_init(
+        integrations=[OpenAIAgentsIntegration()],
+        traces_sample_rate=1.0,
+    )
+
+    # Create a mock model with stream_response and get_response
+    class MockModel:
+        model = "gpt-4"
+
+        async def get_response(self, *args, **kwargs):
+            # Not used in this test, but required by the wrapper
+            pass
+
+        async def stream_response(self, *args, **kwargs):
+            # First event: ResponseCreatedEvent (no delta - should NOT trigger TTFT)
+            created_event = MagicMock(spec=["type", "sequence_number"])
+            created_event.type = "response.created"
+            yield created_event
+
+            # Simulate server-side processing delay before first token
+            await asyncio.sleep(0.05)  # 50ms delay
+
+            # Second event: ResponseTextDeltaEvent (HAS delta - triggers TTFT)
+            text_delta_event = MagicMock(spec=["delta", "type", "content_index"])
+            text_delta_event.delta = "Hello"
+            text_delta_event.type = "response.output_text.delta"
+            yield text_delta_event
+
+            # Third event: more text content (also has delta, but TTFT already recorded)
+            text_delta_event2 = MagicMock(spec=["delta", "type", "content_index"])
+            text_delta_event2.delta = " world!"
+            text_delta_event2.type = "response.output_text.delta"
+            yield text_delta_event2
+
+            # Final event: ResponseCompletedEvent (has response, no delta)
+            completed_event = MagicMock(spec=["response", "type", "sequence_number"])
+            completed_event.response = MagicMock()
+            completed_event.response.model = "gpt-4"
+            completed_event.response.usage = Usage(
+                requests=1,
+                input_tokens=10,
+                output_tokens=5,
+                total_tokens=15,
+            )
+            completed_event.response.output = []
+            yield completed_event
+
+    # Create a mock original _get_model that returns our mock model
+    def mock_get_model(agent, run_config):
+        return MockModel()
+
+    # Wrap it with our integration wrapper
+    wrapped_get_model = _create_get_model_wrapper(mock_get_model)
+
+    with sentry_sdk.start_transaction(name="test_ttft", sampled=True) as transaction:
+        # Get the wrapped model (this applies the stream_response wrapper)
+        wrapped_model = wrapped_get_model(None, test_agent, MagicMock())
+
+        # Call the wrapped stream_response and consume all events
+        async for _event in wrapped_model.stream_response():
+            pass
+
+        # Verify TTFT is recorded on the chat span (must be inside transaction context)
+        chat_spans = [
+            s for s in transaction._span_recorder.spans if s.op == "gen_ai.chat"
+        ]
+        assert len(chat_spans) >= 1
+        chat_span = chat_spans[0]
+
+        assert SPANDATA.GEN_AI_RESPONSE_TIME_TO_FIRST_TOKEN in chat_span._data
+        ttft_value = chat_span._data[SPANDATA.GEN_AI_RESPONSE_TIME_TO_FIRST_TOKEN]
+        # TTFT should be at least 40ms (our simulated delay minus some variance) but reasonable
+        assert 0.04 < ttft_value < 1.0, f"TTFT {ttft_value} should be around 50ms"
+
+        # Verify streaming flag is set
+        assert chat_span._data.get(SPANDATA.GEN_AI_RESPONSE_STREAMING) is True
diff --git a/tests/integrations/pydantic_ai/test_pydantic_ai.py b/tests/integrations/pydantic_ai/test_pydantic_ai.py
index 049bcde39c..f315909ea1 100644
--- a/tests/integrations/pydantic_ai/test_pydantic_ai.py
+++ b/tests/integrations/pydantic_ai/test_pydantic_ai.py
@@ -1,12 +1,21 @@
 import asyncio
+import json
 import pytest
+from unittest.mock import MagicMock
 
 from typing import Annotated
 from pydantic import Field
 
+import sentry_sdk
+from sentry_sdk._types import BLOB_DATA_SUBSTITUTE
+from sentry_sdk.consts import SPANDATA
 from sentry_sdk.integrations.pydantic_ai import PydanticAIIntegration
+from sentry_sdk.integrations.pydantic_ai.spans.ai_client import _set_input_messages
+from sentry_sdk.integrations.pydantic_ai.spans.utils import _set_usage_data
 
 from pydantic_ai import Agent
+from pydantic_ai.messages import BinaryContent, UserPromptPart
+from pydantic_ai.usage import RequestUsage
 from pydantic_ai.models.test import TestModel
 from pydantic_ai.exceptions import ModelRetry, UnexpectedModelBehavior
 
@@ -505,7 +514,18 @@ async def test_model_settings(sentry_init, capture_events, test_agent_with_setti
 
 
 @pytest.mark.asyncio
-async def test_system_prompt_in_messages(sentry_init, capture_events):
+@pytest.mark.parametrize(
+    "send_default_pii, include_prompts",
+    [
+        (True, True),
+        (True, False),
+        (False, True),
+        (False, False),
+    ],
+)
+async def test_system_prompt_attribute(
+    sentry_init, capture_events, send_default_pii, include_prompts
+):
     """
     Test that system prompts are included as the first message.
     """
@@ -516,9 +536,9 @@ async def test_system_prompt_in_messages(sentry_init, capture_events):
     )
 
     sentry_init(
-        integrations=[PydanticAIIntegration()],
+        integrations=[PydanticAIIntegration(include_prompts=include_prompts)],
         traces_sample_rate=1.0,
-        send_default_pii=True,
+        send_default_pii=send_default_pii,
     )
 
     events = capture_events()
@@ -533,12 +553,17 @@ async def test_system_prompt_in_messages(sentry_init, capture_events):
     assert len(chat_spans) >= 1
 
     chat_span = chat_spans[0]
-    messages_str = chat_span["data"]["gen_ai.request.messages"]
 
-    # Messages is serialized as a string
-    # Should contain system role and helpful assistant text
-    assert "system" in messages_str
-    assert "helpful assistant" in messages_str
+    if send_default_pii and include_prompts:
+        system_instructions = chat_span["data"][SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS]
+        assert json.loads(system_instructions) == [
+            {
+                "type": "text",
+                "content": "You are a helpful assistant specialized in testing.",
+            }
+        ]
+    else:
+        assert SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS not in chat_span["data"]
 
 
 @pytest.mark.asyncio
@@ -1175,7 +1200,18 @@ async def test_invoke_agent_with_list_user_prompt(sentry_init, capture_events):
 
 
 @pytest.mark.asyncio
-async def test_invoke_agent_with_instructions(sentry_init, capture_events):
+@pytest.mark.parametrize(
+    "send_default_pii, include_prompts",
+    [
+        (True, True),
+        (True, False),
+        (False, True),
+        (False, False),
+    ],
+)
+async def test_invoke_agent_with_instructions(
+    sentry_init, capture_events, send_default_pii, include_prompts
+):
     """
     Test that invoke_agent span handles instructions correctly.
     """
@@ -1192,9 +1228,9 @@ async def test_invoke_agent_with_instructions(sentry_init, capture_events):
     agent._system_prompts = ["System prompt"]
 
     sentry_init(
-        integrations=[PydanticAIIntegration()],
+        integrations=[PydanticAIIntegration(include_prompts=include_prompts)],
         traces_sample_rate=1.0,
-        send_default_pii=True,
+        send_default_pii=send_default_pii,
     )
 
     events = capture_events()
@@ -1202,14 +1238,22 @@ async def test_invoke_agent_with_instructions(sentry_init, capture_events):
     await agent.run("Test input")
 
     (transaction,) = events
+    spans = transaction["spans"]
 
-    # Check that the invoke_agent transaction has messages data
-    if "gen_ai.request.messages" in transaction["contexts"]["trace"]["data"]:
-        messages_str = transaction["contexts"]["trace"]["data"][
-            "gen_ai.request.messages"
+    # The transaction IS the invoke_agent span, check for messages in chat spans instead
+    chat_spans = [s for s in spans if s["op"] == "gen_ai.chat"]
+    assert len(chat_spans) >= 1
+
+    chat_span = chat_spans[0]
+
+    if send_default_pii and include_prompts:
+        system_instructions = chat_span["data"][SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS]
+        assert json.loads(system_instructions) == [
+            {"type": "text", "content": "System prompt"},
+            {"type": "text", "content": "Instruction 1\nInstruction 2"},
         ]
-        # Should contain both instructions and system prompts
-        assert "Instruction" in messages_str or "System prompt" in messages_str
+    else:
+        assert SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS not in chat_span["data"]
 
 
 @pytest.mark.asyncio
@@ -2604,3 +2648,147 @@ async def test_ai_client_span_gets_agent_from_scope(sentry_init, capture_events)
 
     # Should not crash
     assert transaction is not None
+
+
+def _get_messages_from_span(span_data):
+    """Helper to extract and parse messages from span data."""
+    messages_data = span_data["gen_ai.request.messages"]
+    return (
+        json.loads(messages_data) if isinstance(messages_data, str) else messages_data
+    )
+
+
+def _find_binary_content(messages_data, expected_modality, expected_mime_type):
+    """Helper to find and verify binary content in messages."""
+    for msg in messages_data:
+        if "content" not in msg:
+            continue
+        for content_item in msg["content"]:
+            if content_item.get("type") == "blob":
+                assert content_item["modality"] == expected_modality
+                assert content_item["mime_type"] == expected_mime_type
+                assert content_item["content"] == BLOB_DATA_SUBSTITUTE
+                return True
+    return False
+
+
+@pytest.mark.asyncio
+async def test_binary_content_encoding_image(sentry_init, capture_events):
+    """Test that BinaryContent with image data is properly encoded in messages."""
+    sentry_init(
+        integrations=[PydanticAIIntegration()],
+        traces_sample_rate=1.0,
+        send_default_pii=True,
+    )
+
+    events = capture_events()
+
+    with sentry_sdk.start_transaction(op="test", name="test"):
+        span = sentry_sdk.start_span(op="test_span")
+        binary_content = BinaryContent(
+            data=b"fake_image_data_12345", media_type="image/png"
+        )
+        user_part = UserPromptPart(content=["Look at this image:", binary_content])
+        mock_msg = MagicMock()
+        mock_msg.parts = [user_part]
+        mock_msg.instructions = None
+
+        _set_input_messages(span, [mock_msg])
+        span.finish()
+
+    (event,) = events
+    span_data = event["spans"][0]["data"]
+    messages_data = _get_messages_from_span(span_data)
+    assert _find_binary_content(messages_data, "image", "image/png")
+
+
+@pytest.mark.asyncio
+async def test_binary_content_encoding_mixed_content(sentry_init, capture_events):
+    """Test that BinaryContent mixed with text content is properly handled."""
+    sentry_init(
+        integrations=[PydanticAIIntegration()],
+        traces_sample_rate=1.0,
+        send_default_pii=True,
+    )
+
+    events = capture_events()
+
+    with sentry_sdk.start_transaction(op="test", name="test"):
+        span = sentry_sdk.start_span(op="test_span")
+        binary_content = BinaryContent(
+            data=b"fake_image_bytes", media_type="image/jpeg"
+        )
+        user_part = UserPromptPart(
+            content=["Here is an image:", binary_content, "What do you see?"]
+        )
+        mock_msg = MagicMock()
+        mock_msg.parts = [user_part]
+        mock_msg.instructions = None
+
+        _set_input_messages(span, [mock_msg])
+        span.finish()
+
+    (event,) = events
+    span_data = event["spans"][0]["data"]
+    messages_data = _get_messages_from_span(span_data)
+
+    # Verify both text and binary content are present
+    found_text = any(
+        content_item.get("type") == "text"
+        for msg in messages_data
+        if "content" in msg
+        for content_item in msg["content"]
+    )
+    assert found_text, "Text content should be found"
+    assert _find_binary_content(messages_data, "image", "image/jpeg")
+
+
+@pytest.mark.asyncio
+async def test_binary_content_in_agent_run(sentry_init, capture_events):
+    """Test that BinaryContent in actual agent run is properly captured in spans."""
+    agent = Agent("test", name="test_binary_agent")
+
+    sentry_init(
+        integrations=[PydanticAIIntegration()],
+        traces_sample_rate=1.0,
+        send_default_pii=True,
+    )
+
+    events = capture_events()
+    binary_content = BinaryContent(
+        data=b"fake_image_data_for_testing", media_type="image/png"
+    )
+    await agent.run(["Analyze this image:", binary_content])
+
+    (transaction,) = events
+    chat_spans = [s for s in transaction["spans"] if s["op"] == "gen_ai.chat"]
+    assert len(chat_spans) >= 1
+
+    chat_span = chat_spans[0]
+    if "gen_ai.request.messages" in chat_span["data"]:
+        messages_str = str(chat_span["data"]["gen_ai.request.messages"])
+        assert any(keyword in messages_str for keyword in ["blob", "image", "base64"])
+
+
+@pytest.mark.asyncio
+async def test_set_usage_data_with_cache_tokens(sentry_init, capture_events):
+    """Test that cache_read_tokens and cache_write_tokens are tracked."""
+    sentry_init(integrations=[PydanticAIIntegration()], traces_sample_rate=1.0)
+
+    events = capture_events()
+
+    with sentry_sdk.start_transaction(op="test", name="test"):
+        span = sentry_sdk.start_span(op="test_span")
+        usage = RequestUsage(
+            input_tokens=100,
+            output_tokens=50,
+            cache_read_tokens=80,
+            cache_write_tokens=20,
+        )
+        _set_usage_data(span, usage)
+        span.finish()
+
+    (event,) = events
+    (span_data,) = event["spans"]
+    assert span_data["data"][SPANDATA.GEN_AI_USAGE_INPUT_TOKENS_CACHED] == 80
+    assert span_data["data"][SPANDATA.GEN_AI_USAGE_INPUT_TOKENS_CACHE_WRITE] == 20
diff --git a/tests/integrations/ray/test_ray.py b/tests/integrations/ray/test_ray.py
index dcbf8f456b..be7ebc9d05 100644
--- a/tests/integrations/ray/test_ray.py
+++ b/tests/integrations/ray/test_ray.py
@@ -74,10 +74,29 @@ def read_error_from_log(job_id, ray_temp_dir):
     return error
 
 
+def example_task():
+    with sentry_sdk.start_span(op="task", name="example task step"):
+        ...
+
+    return sentry_sdk.get_client().transport.envelopes
+
+
+# RayIntegration must leave variadic keyword arguments at the end
+def example_task_with_kwargs(**kwargs):
+    with sentry_sdk.start_span(op="task", name="example task step"):
+        ...
+
+    return sentry_sdk.get_client().transport.envelopes
+
+
 @pytest.mark.parametrize(
     "task_options", [{}, {"num_cpus": 0, "memory": 1024 * 1024 * 10}]
 )
-def test_tracing_in_ray_tasks(task_options):
+@pytest.mark.parametrize(
+    "task",
+    [example_task, example_task_with_kwargs],
+)
+def test_tracing_in_ray_tasks(task_options, task):
     setup_sentry()
 
     ray.init(
@@ -87,21 +106,18 @@ def test_tracing_in_ray_tasks(task_options):
         }
     )
 
-    def example_task():
-        with sentry_sdk.start_span(op="task", name="example task step"):
-            ...
-
-        return sentry_sdk.get_client().transport.envelopes
-
     # Setup ray task, calling decorator directly instead of @,
     # to accommodate for test parametrization
     if task_options:
-        example_task = ray.remote(**task_options)(example_task)
+        example_task = ray.remote(**task_options)(task)
     else:
-        example_task = ray.remote(example_task)
+        example_task = ray.remote(task)
 
     # Function name shouldn't be overwritten by Sentry wrapper
-    assert example_task._function_name == "tests.integrations.ray.test_ray.example_task"
+    assert (
+        example_task._function_name
+        == f"tests.integrations.ray.test_ray.{task.__name__}"
+    )
 
     with sentry_sdk.start_transaction(op="task", name="ray test transaction"):
         worker_envelopes = ray.get(example_task.remote())
@@ -115,17 +131,14 @@ def example_task():
     worker_transaction = worker_envelope.get_transaction_event()
     assert (
         worker_transaction["transaction"]
-        == "tests.integrations.ray.test_ray.test_tracing_in_ray_tasks.<locals>.example_task"
+        == f"tests.integrations.ray.test_ray.{task.__name__}"
     )
     assert worker_transaction["transaction_info"] == {"source": "task"}
 
     (span,) = client_transaction["spans"]
     assert span["op"] == "queue.submit.ray"
     assert span["origin"] == "auto.queue.ray"
-    assert (
-        span["description"]
-        == "tests.integrations.ray.test_ray.test_tracing_in_ray_tasks.<locals>.example_task"
-    )
+    assert span["description"] == f"tests.integrations.ray.test_ray.{task.__name__}"
     assert span["parent_span_id"] == client_transaction["contexts"]["trace"]["span_id"]
     assert span["trace_id"] == client_transaction["contexts"]["trace"]["trace_id"]
 
diff --git a/tests/integrations/stdlib/test_httplib.py b/tests/integrations/stdlib/test_httplib.py
index 588c3b34f4..ad6b0688b9 100644
--- a/tests/integrations/stdlib/test_httplib.py
+++ b/tests/integrations/stdlib/test_httplib.py
@@ -1,7 +1,10 @@
 import os
 import datetime
+import socket
 from http.client import HTTPConnection, HTTPSConnection
+from http.server import BaseHTTPRequestHandler, HTTPServer
 from socket import SocketIO
+from threading import Thread
 from urllib.error import HTTPError
 from urllib.request import urlopen
 from unittest import mock
@@ -12,11 +15,35 @@
 from sentry_sdk.consts import MATCH_ALL, SPANDATA
 from sentry_sdk.integrations.stdlib import StdlibIntegration
 
-from tests.conftest import ApproxDict, create_mock_http_server
+from tests.conftest import ApproxDict, create_mock_http_server, get_free_port
 
 PORT = create_mock_http_server()
 
 
+class MockProxyRequestHandler(BaseHTTPRequestHandler):
+    def do_CONNECT(self):
+        self.send_response(200, "Connection Established")
+        self.end_headers()
+
+        self.rfile.readline()
+
+        response = b"HTTP/1.1 200 OK\r\nContent-Length: 0\r\n\r\n"
+        self.wfile.write(response)
+        self.wfile.flush()
+
+
+def create_mock_proxy_server():
+    proxy_port = get_free_port()
+    proxy_server = HTTPServer(("localhost", proxy_port), MockProxyRequestHandler)
+    proxy_thread = Thread(target=proxy_server.serve_forever)
+    proxy_thread.daemon = True
+    proxy_thread.start()
+    return proxy_port
+
+
+PROXY_PORT = create_mock_proxy_server()
+
+
 def test_crumb_capture(sentry_init, capture_events):
     sentry_init(integrations=[StdlibIntegration()])
     events = capture_events()
@@ -642,3 +669,25 @@ def test_http_timeout(monkeypatch, sentry_init, capture_envelopes):
     span = transaction["spans"][0]
     assert span["op"] == "http.client"
     assert span["description"] == f"GET http://localhost:{PORT}/bla"  # noqa: E231
+
+
+@pytest.mark.parametrize("tunnel_port", [8080, None])
+def test_proxy_http_tunnel(sentry_init, capture_events, tunnel_port):
+    sentry_init(traces_sample_rate=1.0)
+    events = capture_events()
+
+    with start_transaction(name="test_transaction"):
+        conn = HTTPConnection("localhost", PROXY_PORT)
+        conn.set_tunnel("api.example.com", tunnel_port)
+        conn.request("GET", "/foo")
+        conn.getresponse()
+
+    (event,) = events
+    (span,) = event["spans"]
+
+    port_modifier = f":{tunnel_port}" if tunnel_port else ""
+    assert span["description"] == f"GET http://api.example.com{port_modifier}/foo"
+    assert span["data"]["url"] == f"http://api.example.com{port_modifier}/foo"
+    assert span["data"][SPANDATA.HTTP_METHOD] == "GET"
+    assert span["data"][SPANDATA.NETWORK_PEER_ADDRESS] == "localhost"
+    assert span["data"][SPANDATA.NETWORK_PEER_PORT] == PROXY_PORT
diff --git a/tests/test_ai_integration_deactivation.py b/tests/test_ai_integration_deactivation.py
index dc8aef6be8..b02b64c6ee 100644
--- a/tests/test_ai_integration_deactivation.py
+++ b/tests/test_ai_integration_deactivation.py
@@ -57,6 +57,7 @@ def test_integration_deactivates_map_exists():
     assert "langchain" in _INTEGRATION_DEACTIVATES
     assert "openai" in _INTEGRATION_DEACTIVATES["langchain"]
     assert "anthropic" in _INTEGRATION_DEACTIVATES["langchain"]
+    assert "google_genai" in _INTEGRATION_DEACTIVATES["langchain"]
     assert "openai_agents" in _INTEGRATION_DEACTIVATES
     assert "openai" in _INTEGRATION_DEACTIVATES["openai_agents"]
     assert "pydantic_ai" in _INTEGRATION_DEACTIVATES
diff --git a/tests/test_ai_monitoring.py b/tests/test_ai_monitoring.py
index 8d3d4ba204..969d14658d 100644
--- a/tests/test_ai_monitoring.py
+++ b/tests/test_ai_monitoring.py
@@ -4,7 +4,11 @@
 import pytest
 
 import sentry_sdk
-from sentry_sdk._types import AnnotatedValue
+from sentry_sdk._types import (
+    AnnotatedValue,
+    SENSITIVE_DATA_SUBSTITUTE,
+    BLOB_DATA_SUBSTITUTE,
+)
 from sentry_sdk.ai.monitoring import ai_track
 from sentry_sdk.ai.utils import (
     MAX_GEN_AI_MESSAGE_BYTES,
@@ -13,6 +17,15 @@
     truncate_and_annotate_messages,
     truncate_messages_by_size,
     _find_truncation_index,
+    parse_data_uri,
+    redact_blob_message_parts,
+    get_modality_from_mime_type,
+    transform_openai_content_part,
+    transform_anthropic_content_part,
+    transform_google_content_part,
+    transform_generic_content_part,
+    transform_content_part,
+    transform_message_content,
 )
 from sentry_sdk.serializer import serialize
 from sentry_sdk.utils import safe_serialize
@@ -307,7 +320,7 @@ def test_single_message_truncation(self):
 
 
 class TestTruncateAndAnnotateMessages:
-    def test_no_truncation_returns_list(self, sample_messages):
+    def test_only_keeps_last_message(self, sample_messages):
         class MockSpan:
             def __init__(self):
                 self.span_id = "test_span_id"
@@ -326,9 +339,8 @@ def __init__(self):
 
         assert isinstance(result, list)
         assert not isinstance(result, AnnotatedValue)
-        assert len(result) == len(sample_messages)
-        assert result == sample_messages
-        assert span.span_id not in scope._gen_ai_original_message_count
+        assert len(result) == 1
+        assert result[0] == sample_messages[-1]
 
     def test_truncation_sets_metadata_on_scope(self, large_messages):
         class MockSpan:
@@ -348,7 +360,7 @@ def __init__(self):
         scope = MockScope()
         original_count = len(large_messages)
         result = truncate_and_annotate_messages(
-            large_messages, span, scope, max_bytes=small_limit
+            large_messages, span, scope, max_single_message_chars=small_limit
         )
 
         assert isinstance(result, list)
@@ -375,7 +387,7 @@ def __init__(self):
         scope = MockScope()
 
         result = truncate_and_annotate_messages(
-            large_messages, span, scope, max_bytes=small_limit
+            large_messages, span, scope, max_single_message_chars=small_limit
         )
 
         assert scope._gen_ai_original_message_count[span.span_id] == original_count
@@ -419,12 +431,55 @@ def __init__(self):
         span = MockSpan()
         scope = MockScope()
         result = truncate_and_annotate_messages(
-            large_messages, span, scope, max_bytes=small_limit
+            large_messages, span, scope, max_single_message_chars=small_limit
         )
 
         assert isinstance(result, list)
         assert result[0] == large_messages[-len(result)]
 
+    def test_preserves_original_messages_with_blobs(self):
+        """Test that truncate_and_annotate_messages doesn't mutate the original messages"""
+
+        class MockSpan:
+            def __init__(self):
+                self.span_id = "test_span_id"
+                self.data = {}
+
+            def set_data(self, key, value):
+                self.data[key] = value
+
+        class MockScope:
+            def __init__(self):
+                self._gen_ai_original_message_count = {}
+
+        messages = [
+            {
+                "role": "user",
+                "content": [
+                    {"text": "What's in this image?", "type": "text"},
+                    {
+                        "type": "blob",
+                        "modality": "image",
+                        "content": "data:image/jpeg;base64,original_content",
+                    },
+                ],
+            }
+        ]
+
+        original_blob_content = messages[0]["content"][1]["content"]
+
+        span = MockSpan()
+        scope = MockScope()
+
+        # This should NOT mutate the original messages
+        result = truncate_and_annotate_messages(messages, span, scope)
+
+        # Verify original is unchanged
+        assert messages[0]["content"][1]["content"] == original_blob_content
+
+        # Verify result has redacted content
+        assert result[0]["content"][1]["content"] == BLOB_DATA_SUBSTITUTE
+
 
 class TestClientAnnotation:
     def test_client_wraps_truncated_messages_in_annotated_value(self, large_messages):
@@ -451,7 +506,7 @@ def __init__(self):
 
         # Simulate what integrations do
         truncated_messages = truncate_and_annotate_messages(
-            large_messages, span, scope, max_bytes=small_limit
+            large_messages, span, scope, max_single_message_chars=small_limit
         )
         span.set_data(SPANDATA.GEN_AI_REQUEST_MESSAGES, truncated_messages)
 
@@ -507,7 +562,7 @@ def __init__(self):
         original_message_count = len(large_messages)
 
         truncated_messages = truncate_and_annotate_messages(
-            large_messages, span, scope, max_bytes=small_limit
+            large_messages, span, scope, max_single_message_chars=small_limit
         )
 
         assert len(truncated_messages) < original_message_count
@@ -542,3 +597,1157 @@ def __init__(self):
         assert isinstance(messages_value, AnnotatedValue)
         assert messages_value.metadata["len"] == stored_original_length
         assert len(messages_value.value) == len(truncated_messages)
+
+
+class TestRedactBlobMessageParts:
+    def test_redacts_single_blob_content(self):
+        """Test that blob content is redacted without mutating original messages"""
+        messages = [
+            {
+                "role": "user",
+                "content": [
+                    {
+                        "text": "How many ponies do you see in the image?",
+                        "type": "text",
+                    },
+                    {
+                        "type": "blob",
+                        "modality": "image",
+                        "mime_type": "image/jpeg",
+                        "content": "data:image/jpeg;base64,/9j/4AAQSkZJRg==",
+                    },
+                ],
+            }
+        ]
+
+        # Save original blob content for comparison
+        original_blob_content = messages[0]["content"][1]["content"]
+
+        result = redact_blob_message_parts(messages)
+
+        # Original messages should be UNCHANGED
+        assert messages[0]["content"][1]["content"] == original_blob_content
+
+        # Result should have redacted content
+        assert (
+            result[0]["content"][0]["text"]
+            == "How many ponies do you see in the image?"
+        )
+        assert result[0]["content"][0]["type"] == "text"
+        assert result[0]["content"][1]["type"] == "blob"
+        assert result[0]["content"][1]["modality"] == "image"
+        assert result[0]["content"][1]["mime_type"] == "image/jpeg"
+        assert result[0]["content"][1]["content"] == BLOB_DATA_SUBSTITUTE
+
+    def test_redacts_multiple_blob_parts(self):
+        """Test that multiple blob parts are redacted without mutation"""
+        messages = [
+            {
+                "role": "user",
+                "content": [
+                    {"text": "Compare these images", "type": "text"},
+                    {
+                        "type": "blob",
+                        "modality": "image",
+                        "mime_type": "image/jpeg",
+                        "content": "data:image/jpeg;base64,first_image",
+                    },
+                    {
+                        "type": "blob",
+                        "modality": "image",
+                        "mime_type": "image/png",
+                        "content": "data:image/png;base64,second_image",
+                    },
+                ],
+            }
+        ]
+
+        original_first = messages[0]["content"][1]["content"]
+        original_second = messages[0]["content"][2]["content"]
+
+        result = redact_blob_message_parts(messages)
+
+        # Original should be unchanged
+        assert messages[0]["content"][1]["content"] == original_first
+        assert messages[0]["content"][2]["content"] == original_second
+
+        # Result should be redacted
+        assert result[0]["content"][0]["text"] == "Compare these images"
+        assert result[0]["content"][1]["content"] == BLOB_DATA_SUBSTITUTE
+        assert result[0]["content"][2]["content"] == BLOB_DATA_SUBSTITUTE
+
+    def test_redacts_blobs_in_multiple_messages(self):
+        """Test that blob parts are redacted across multiple messages without mutation"""
+        messages = [
+            {
+                "role": "user",
+                "content": [
+                    {"text": "First message", "type": "text"},
+                    {
+                        "type": "blob",
+                        "modality": "image",
+                        "content": "data:image/jpeg;base64,first",
+                    },
+                ],
+            },
+            {
+                "role": "assistant",
+                "content": "I see the image.",
+            },
+            {
+                "role": "user",
+                "content": [
+                    {"text": "Second message", "type": "text"},
+                    {
+                        "type": "blob",
+                        "modality": "image",
+                        "content": "data:image/jpeg;base64,second",
+                    },
+                ],
+            },
+        ]
+
+        original_first = messages[0]["content"][1]["content"]
+        original_second = messages[2]["content"][1]["content"]
+
+        result = redact_blob_message_parts(messages)
+
+        # Original should be unchanged
+        assert messages[0]["content"][1]["content"] == original_first
+        assert messages[2]["content"][1]["content"] == original_second
+
+        # Result should be redacted
+        assert result[0]["content"][1]["content"] == BLOB_DATA_SUBSTITUTE
+        assert result[1]["content"] == "I see the image."  # Unchanged
+        assert result[2]["content"][1]["content"] == BLOB_DATA_SUBSTITUTE
+
+    def test_no_blobs_returns_original_list(self):
+        """Test that messages without blobs are returned as-is (performance optimization)"""
+        messages = [
+            {"role": "user", "content": "Simple text message"},
+            {"role": "assistant", "content": "Simple response"},
+        ]
+
+        result = redact_blob_message_parts(messages)
+
+        # Should return the same list object when no blobs present
+        assert result is messages
+
+    def test_handles_non_dict_messages(self):
+        """Test that non-dict messages are handled gracefully"""
+        messages = [
+            "string message",
+            {"role": "user", "content": "text"},
+            None,
+            123,
+        ]
+
+        result = redact_blob_message_parts(messages)
+
+        # Should return same list since no blobs
+        assert result is messages
+
+    def test_handles_non_dict_content_items(self):
+        """Test that non-dict content items in arrays are handled"""
+        messages = [
+            {
+                "role": "user",
+                "content": [
+                    "string item",
+                    {"text": "text item", "type": "text"},
+                    None,
+                ],
+            }
+        ]
+
+        result = redact_blob_message_parts(messages)
+
+        # Should return same list since no blobs
+        assert result is messages
+
+
+class TestParseDataUri:
+    def test_parses_base64_image_data_uri(self):
+        """Test parsing a standard base64-encoded image data URI"""
+        uri = "data:image/jpeg;base64,/9j/4AAQSkZJRg=="
+        mime_type, content = parse_data_uri(uri)
+
+        assert mime_type == "image/jpeg"
+        assert content == "/9j/4AAQSkZJRg=="
+
+    def test_parses_png_data_uri(self):
+        """Test parsing a PNG image data URI"""
+        uri = "data:image/png;base64,iVBORw0KGgo="
+        mime_type, content = parse_data_uri(uri)
+
+        assert mime_type == "image/png"
+        assert content == "iVBORw0KGgo="
+
+    def test_parses_plain_text_data_uri(self):
+        """Test parsing a plain text data URI without base64 encoding"""
+        uri = "data:text/plain,Hello World"
+        mime_type, content = parse_data_uri(uri)
+
+        assert mime_type == "text/plain"
+        assert content == "Hello World"
+
+    def test_parses_data_uri_with_empty_mime_type(self):
+        """Test parsing a data URI with empty mime type"""
+        uri = "data:;base64,SGVsbG8="
+        mime_type, content = parse_data_uri(uri)
+
+        assert mime_type == ""
+        assert content == "SGVsbG8="
+
+    def test_parses_data_uri_with_only_data_prefix(self):
+        """Test parsing a data URI with only the data: prefix and content"""
+        uri = "data:,Hello"
+        mime_type, content = parse_data_uri(uri)
+
+        assert mime_type == ""
+        assert content == "Hello"
+
+    def test_raises_on_missing_comma(self):
+        """Test that ValueError is raised when comma separator is missing"""
+        with pytest.raises(ValueError, match="missing comma separator"):
+            parse_data_uri("data:image/jpeg;base64")
+
+    def test_raises_on_empty_string(self):
+        """Test that ValueError is raised for empty string"""
+        with pytest.raises(ValueError, match="missing comma separator"):
+            parse_data_uri("")
+
+    def test_handles_content_with_commas(self):
+        """Test that only the first comma is used as separator"""
+        uri = "data:text/plain,Hello,World,With,Commas"
+        mime_type, content = parse_data_uri(uri)
+
+        assert mime_type == "text/plain"
+        assert content == "Hello,World,With,Commas"
+
+    def test_parses_data_uri_with_multiple_parameters(self):
+        """Test parsing a data URI with multiple parameters in header"""
+        uri = "data:text/plain;charset=utf-8;base64,SGVsbG8="
+        mime_type, content = parse_data_uri(uri)
+
+        assert mime_type == "text/plain"
+        assert content == "SGVsbG8="
+
+    def test_parses_audio_data_uri(self):
+        """Test parsing an audio data URI"""
+        uri = "data:audio/wav;base64,UklGRiQA"
+        mime_type, content = parse_data_uri(uri)
+
+        assert mime_type == "audio/wav"
+        assert content == "UklGRiQA"
+
+    def test_handles_uri_without_data_prefix(self):
+        """Test parsing a URI that doesn't have the data: prefix"""
+        uri = "image/jpeg;base64,/9j/4AAQ"
+        mime_type, content = parse_data_uri(uri)
+
+        assert mime_type == "image/jpeg"
+        assert content == "/9j/4AAQ"
+
+
+class TestGetModalityFromMimeType:
+    def test_image_mime_types(self):
+        """Test that image MIME types return 'image' modality"""
+        assert get_modality_from_mime_type("image/jpeg") == "image"
+        assert get_modality_from_mime_type("image/png") == "image"
+        assert get_modality_from_mime_type("image/gif") == "image"
+        assert get_modality_from_mime_type("image/webp") == "image"
+        assert get_modality_from_mime_type("IMAGE/JPEG") == "image"  # case insensitive
+
+    def test_audio_mime_types(self):
+        """Test that audio MIME types return 'audio' modality"""
+        assert get_modality_from_mime_type("audio/mp3") == "audio"
+        assert get_modality_from_mime_type("audio/wav") == "audio"
+        assert get_modality_from_mime_type("audio/ogg") == "audio"
+        assert get_modality_from_mime_type("AUDIO/MP3") == "audio"  # case insensitive
+
+    def test_video_mime_types(self):
+        """Test that video MIME types return 'video' modality"""
+        assert get_modality_from_mime_type("video/mp4") == "video"
+        assert get_modality_from_mime_type("video/webm") == "video"
+        assert get_modality_from_mime_type("video/quicktime") == "video"
+        assert get_modality_from_mime_type("VIDEO/MP4") == "video"  # case insensitive
+
+    def test_document_mime_types(self):
+        """Test that application and text MIME types return 'document' modality"""
+        assert get_modality_from_mime_type("application/pdf") == "document"
+        assert get_modality_from_mime_type("application/json") == "document"
+        assert get_modality_from_mime_type("text/plain") == "document"
+        assert get_modality_from_mime_type("text/html") == "document"
+
+    def test_empty_mime_type_returns_image(self):
+        """Test that empty MIME type defaults to 'image'"""
+        assert get_modality_from_mime_type("") == "image"
+
+    def test_none_mime_type_returns_image(self):
+        """Test that None-like values default to 'image'"""
+        assert get_modality_from_mime_type(None) == "image"
+
+    def test_unknown_mime_type_returns_image(self):
+        """Test that unknown MIME types default to 'image'"""
+        assert get_modality_from_mime_type("unknown/type") == "image"
+        assert get_modality_from_mime_type("custom/format") == "image"
+
+
+class TestTransformOpenAIContentPart:
+    """Tests for the OpenAI-specific transform function."""
+
+    def test_image_url_with_data_uri(self):
+        """Test transforming OpenAI image_url with base64 data URI"""
+        content_part = {
+            "type": "image_url",
+            "image_url": {"url": "data:image/jpeg;base64,/9j/4AAQSkZJRg=="},
+        }
+        result = transform_openai_content_part(content_part)
+
+        assert result == {
+            "type": "blob",
+            "modality": "image",
+            "mime_type": "image/jpeg",
+            "content": "/9j/4AAQSkZJRg==",
+        }
+
+    def test_image_url_with_regular_url(self):
+        """Test transforming OpenAI image_url with regular URL"""
+        content_part = {
+            "type": "image_url",
+            "image_url": {"url": "https://example.com/image.jpg"},
+        }
+        result = transform_openai_content_part(content_part)
+
+        assert result == {
+            "type": "uri",
+            "modality": "image",
+            "mime_type": "",
+            "uri": "https://example.com/image.jpg",
+        }
+
+    def test_image_url_string_format(self):
+        """Test transforming OpenAI image_url where image_url is a string"""
+        content_part = {
+            "type": "image_url",
+            "image_url": "https://example.com/image.jpg",
+        }
+        result = transform_openai_content_part(content_part)
+
+        assert result == {
+            "type": "uri",
+            "modality": "image",
+            "mime_type": "",
+            "uri": "https://example.com/image.jpg",
+        }
+
+    def test_image_url_invalid_data_uri(self):
+        """Test transforming OpenAI image_url with invalid data URI falls back to URI"""
+        content_part = {
+            "type": "image_url",
+            "image_url": {"url": "data:image/jpeg;base64"},  # Missing comma
+        }
+        result = transform_openai_content_part(content_part)
+
+        assert result == {
+            "type": "uri",
+            "modality": "image",
+            "mime_type": "",
+            "uri": "data:image/jpeg;base64",
+        }
+
+    def test_empty_url_returns_none(self):
+        """Test that image_url with empty URL returns None"""
+        content_part = {"type": "image_url", "image_url": {"url": ""}}
+        assert transform_openai_content_part(content_part) is None
+
+    def test_non_image_url_type_returns_none(self):
+        """Test that non-image_url types return None"""
+        content_part = {"type": "text", "text": "Hello"}
+        assert transform_openai_content_part(content_part) is None
+
+    def test_anthropic_format_returns_none(self):
+        """Test that Anthropic format returns None (not handled)"""
+        content_part = {
+            "type": "image",
+            "source": {"type": "base64", "media_type": "image/png", "data": "abc"},
+        }
+        assert transform_openai_content_part(content_part) is None
+
+    def test_google_format_returns_none(self):
+        """Test that Google format returns None (not handled)"""
+        content_part = {"inline_data": {"mime_type": "image/jpeg", "data": "abc"}}
+        assert transform_openai_content_part(content_part) is None
+
+    def test_non_dict_returns_none(self):
+        """Test that non-dict input returns None"""
+        assert transform_openai_content_part("string") is None
+        assert transform_openai_content_part(123) is None
+        assert transform_openai_content_part(None) is None
+
+
+class TestTransformAnthropicContentPart:
+    """Tests for the Anthropic-specific transform function."""
+
+    def test_image_base64(self):
+        """Test transforming Anthropic image with base64 source"""
+        content_part = {
+            "type": "image",
+            "source": {
+                "type": "base64",
+                "media_type": "image/png",
+                "data": "iVBORw0KGgo=",
+            },
+        }
+        result = transform_anthropic_content_part(content_part)
+
+        assert result == {
+            "type": "blob",
+            "modality": "image",
+            "mime_type": "image/png",
+            "content": "iVBORw0KGgo=",
+        }
+
+    def test_image_url(self):
+        """Test transforming Anthropic image with URL source"""
+        content_part = {
+            "type": "image",
+            "source": {
+                "type": "url",
+                "media_type": "image/jpeg",
+                "url": "https://example.com/image.jpg",
+            },
+        }
+        result = transform_anthropic_content_part(content_part)
+
+        assert result == {
+            "type": "uri",
+            "modality": "image",
+            "mime_type": "image/jpeg",
+            "uri": "https://example.com/image.jpg",
+        }
+
+    def test_image_file(self):
+        """Test transforming Anthropic image with file source"""
+        content_part = {
+            "type": "image",
+            "source": {
+                "type": "file",
+                "media_type": "image/jpeg",
+                "file_id": "file_123",
+            },
+        }
+        result = transform_anthropic_content_part(content_part)
+
+        assert result == {
+            "type": "file",
+            "modality": "image",
+            "mime_type": "image/jpeg",
+            "file_id": "file_123",
+        }
+
+    def test_document_base64(self):
+        """Test transforming Anthropic document with base64 source"""
+        content_part = {
+            "type": "document",
+            "source": {
+                "type": "base64",
+                "media_type": "application/pdf",
+                "data": "JVBERi0xLjQ=",
+            },
+        }
+        result = transform_anthropic_content_part(content_part)
+
+        assert result == {
+            "type": "blob",
+            "modality": "document",
+            "mime_type": "application/pdf",
+            "content": "JVBERi0xLjQ=",
+        }
+
+    def test_document_url(self):
+        """Test transforming Anthropic document with URL source"""
+        content_part = {
+            "type": "document",
+            "source": {
+                "type": "url",
+                "media_type": "application/pdf",
+                "url": "https://example.com/doc.pdf",
+            },
+        }
+        result = transform_anthropic_content_part(content_part)
+
+        assert result == {
+            "type": "uri",
+            "modality": "document",
+            "mime_type": "application/pdf",
+            "uri": "https://example.com/doc.pdf",
+        }
+
+    def test_invalid_source_returns_none(self):
+        """Test that Anthropic format with invalid source returns None"""
+        content_part = {"type": "image", "source": "not_a_dict"}
+        assert transform_anthropic_content_part(content_part) is None
+
+    def test_unknown_source_type_returns_none(self):
+        """Test that Anthropic format with unknown source type returns None"""
+        content_part = {
+            "type": "image",
+            "source": {"type": "unknown", "data": "something"},
+        }
+        assert transform_anthropic_content_part(content_part) is None
+
+    def test_missing_source_returns_none(self):
+        """Test that Anthropic format without source returns None"""
+        content_part = {"type": "image", "data": "something"}
+        assert transform_anthropic_content_part(content_part) is None
+
+    def test_openai_format_returns_none(self):
+        """Test that OpenAI format returns None (not handled)"""
+        content_part = {
+            "type": "image_url",
+            "image_url": {"url": "https://example.com"},
+        }
+        assert transform_anthropic_content_part(content_part) is None
+
+    def test_google_format_returns_none(self):
+        """Test that Google format returns None (not handled)"""
+        content_part = {"inline_data": {"mime_type": "image/jpeg", "data": "abc"}}
+        assert transform_anthropic_content_part(content_part) is None
+
+    def test_non_dict_returns_none(self):
+        """Test that non-dict input returns None"""
+        assert transform_anthropic_content_part("string") is None
+        assert transform_anthropic_content_part(123) is None
+        assert transform_anthropic_content_part(None) is None
+
+
+class TestTransformGoogleContentPart:
+    """Tests for the Google GenAI-specific transform function."""
+
+    def test_inline_data(self):
+        """Test transforming Google inline_data format"""
+        content_part = {
+            "inline_data": {
+                "mime_type": "image/jpeg",
+                "data": "/9j/4AAQSkZJRg==",
+            }
+        }
+        result = transform_google_content_part(content_part)
+
+        assert result == {
+            "type": "blob",
+            "modality": "image",
+            "mime_type": "image/jpeg",
+            "content": "/9j/4AAQSkZJRg==",
+        }
+
+    def test_file_data(self):
+        """Test transforming Google file_data format"""
+        content_part = {
+            "file_data": {
+                "mime_type": "video/mp4",
+                "file_uri": "gs://bucket/video.mp4",
+            }
+        }
+        result = transform_google_content_part(content_part)
+
+        assert result == {
+            "type": "uri",
+            "modality": "video",
+            "mime_type": "video/mp4",
+            "uri": "gs://bucket/video.mp4",
+        }
+
+    def test_inline_data_audio(self):
+        """Test transforming Google inline_data with audio"""
+        content_part = {
+            "inline_data": {
+                "mime_type": "audio/wav",
+                "data": "UklGRiQA",
+            }
+        }
+        result = transform_google_content_part(content_part)
+
+        assert result == {
+            "type": "blob",
+            "modality": "audio",
+            "mime_type": "audio/wav",
+            "content": "UklGRiQA",
+        }
+
+    def test_inline_data_not_dict_returns_none(self):
+        """Test that Google inline_data with non-dict value returns None"""
+        content_part = {"inline_data": "not_a_dict"}
+        assert transform_google_content_part(content_part) is None
+
+    def test_file_data_not_dict_returns_none(self):
+        """Test that Google file_data with non-dict value returns None"""
+        content_part = {"file_data": "not_a_dict"}
+        assert transform_google_content_part(content_part) is None
+
+    def test_openai_format_returns_none(self):
+        """Test that OpenAI format returns None (not handled)"""
+        content_part = {
+            "type": "image_url",
+            "image_url": {"url": "https://example.com"},
+        }
+        assert transform_google_content_part(content_part) is None
+
+    def test_anthropic_format_returns_none(self):
+        """Test that Anthropic format returns None (not handled)"""
+        content_part = {
+            "type": "image",
+            "source": {"type": "base64", "media_type": "image/png", "data": "abc"},
+        }
+        assert transform_google_content_part(content_part) is None
+
+    def test_non_dict_returns_none(self):
+        """Test that non-dict input returns None"""
+        assert transform_google_content_part("string") is None
+        assert transform_google_content_part(123) is None
+        assert transform_google_content_part(None) is None
+
+
+class TestTransformGenericContentPart:
+    """Tests for the generic/LangChain-style transform function."""
+
+    def test_image_base64(self):
+        """Test transforming generic format with base64"""
+        content_part = {
+            "type": "image",
+            "base64": "/9j/4AAQSkZJRg==",
+            "mime_type": "image/jpeg",
+        }
+        result = transform_generic_content_part(content_part)
+
+        assert result == {
+            "type": "blob",
+            "modality": "image",
+            "mime_type": "image/jpeg",
+            "content": "/9j/4AAQSkZJRg==",
+        }
+
+    def test_audio_url(self):
+        """Test transforming generic format with URL"""
+        content_part = {
+            "type": "audio",
+            "url": "https://example.com/audio.mp3",
+            "mime_type": "audio/mp3",
+        }
+        result = transform_generic_content_part(content_part)
+
+        assert result == {
+            "type": "uri",
+            "modality": "audio",
+            "mime_type": "audio/mp3",
+            "uri": "https://example.com/audio.mp3",
+        }
+
+    def test_file_with_file_id(self):
+        """Test transforming generic format with file_id"""
+        content_part = {
+            "type": "file",
+            "file_id": "file_456",
+            "mime_type": "application/pdf",
+        }
+        result = transform_generic_content_part(content_part)
+
+        assert result == {
+            "type": "file",
+            "modality": "document",
+            "mime_type": "application/pdf",
+            "file_id": "file_456",
+        }
+
+    def test_video_base64(self):
+        """Test transforming generic video format"""
+        content_part = {
+            "type": "video",
+            "base64": "AAAA",
+            "mime_type": "video/mp4",
+        }
+        result = transform_generic_content_part(content_part)
+
+        assert result == {
+            "type": "blob",
+            "modality": "video",
+            "mime_type": "video/mp4",
+            "content": "AAAA",
+        }
+
+    def test_image_with_source_returns_none(self):
+        """Test that image with source key (Anthropic style) returns None"""
+        # This is Anthropic format, should NOT be handled by generic
+        content_part = {
+            "type": "image",
+            "source": {"type": "base64", "data": "abc"},
+        }
+        assert transform_generic_content_part(content_part) is None
+
+    def test_text_type_returns_none(self):
+        """Test that text type returns None"""
+        content_part = {"type": "text", "text": "Hello"}
+        assert transform_generic_content_part(content_part) is None
+
+    def test_openai_format_returns_none(self):
+        """Test that OpenAI format returns None (not handled)"""
+        content_part = {
+            "type": "image_url",
+            "image_url": {"url": "https://example.com"},
+        }
+        assert transform_generic_content_part(content_part) is None
+
+    def test_google_format_returns_none(self):
+        """Test that Google format returns None (not handled)"""
+        content_part = {"inline_data": {"mime_type": "image/jpeg", "data": "abc"}}
+        assert transform_generic_content_part(content_part) is None
+
+    def test_non_dict_returns_none(self):
+        """Test that non-dict input returns None"""
+        assert transform_generic_content_part("string") is None
+        assert transform_generic_content_part(123) is None
+        assert transform_generic_content_part(None) is None
+
+    def test_missing_data_key_returns_none(self):
+        """Test that missing data key (base64/url/file_id) returns None"""
+        content_part = {"type": "image", "mime_type": "image/jpeg"}
+        assert transform_generic_content_part(content_part) is None
+
+
+class TestTransformContentPart:
+    # OpenAI/LiteLLM format tests
+    def test_openai_image_url_with_data_uri(self):
+        """Test transforming OpenAI image_url with base64 data URI"""
+        content_part = {
+            "type": "image_url",
+            "image_url": {"url": "data:image/jpeg;base64,/9j/4AAQSkZJRg=="},
+        }
+        result = transform_content_part(content_part)
+
+        assert result == {
+            "type": "blob",
+            "modality": "image",
+            "mime_type": "image/jpeg",
+            "content": "/9j/4AAQSkZJRg==",
+        }
+
+    def test_openai_image_url_with_regular_url(self):
+        """Test transforming OpenAI image_url with regular URL"""
+        content_part = {
+            "type": "image_url",
+            "image_url": {"url": "https://example.com/image.jpg"},
+        }
+        result = transform_content_part(content_part)
+
+        assert result == {
+            "type": "uri",
+            "modality": "image",
+            "mime_type": "",
+            "uri": "https://example.com/image.jpg",
+        }
+
+    def test_openai_image_url_string_format(self):
+        """Test transforming OpenAI image_url where image_url is a string"""
+        content_part = {
+            "type": "image_url",
+            "image_url": "https://example.com/image.jpg",
+        }
+        result = transform_content_part(content_part)
+
+        assert result == {
+            "type": "uri",
+            "modality": "image",
+            "mime_type": "",
+            "uri": "https://example.com/image.jpg",
+        }
+
+    def test_openai_image_url_invalid_data_uri(self):
+        """Test transforming OpenAI image_url with invalid data URI falls back to URI"""
+        content_part = {
+            "type": "image_url",
+            "image_url": {"url": "data:image/jpeg;base64"},  # Missing comma
+        }
+        result = transform_content_part(content_part)
+
+        assert result == {
+            "type": "uri",
+            "modality": "image",
+            "mime_type": "",
+            "uri": "data:image/jpeg;base64",
+        }
+
+    # Anthropic format tests
+    def test_anthropic_image_base64(self):
+        """Test transforming Anthropic image with base64 source"""
+        content_part = {
+            "type": "image",
+            "source": {
+                "type": "base64",
+                "media_type": "image/png",
+                "data": "iVBORw0KGgo=",
+            },
+        }
+        result = transform_content_part(content_part)
+
+        assert result == {
+            "type": "blob",
+            "modality": "image",
+            "mime_type": "image/png",
+            "content": "iVBORw0KGgo=",
+        }
+
+    def test_anthropic_image_url(self):
+        """Test transforming Anthropic image with URL source"""
+        content_part = {
+            "type": "image",
+            "source": {
+                "type": "url",
+                "media_type": "image/jpeg",
+                "url": "https://example.com/image.jpg",
+            },
+        }
+        result = transform_content_part(content_part)
+
+        assert result == {
+            "type": "uri",
+            "modality": "image",
+            "mime_type": "image/jpeg",
+            "uri": "https://example.com/image.jpg",
+        }
+
+    def test_anthropic_image_file(self):
+        """Test transforming Anthropic image with file source"""
+        content_part = {
+            "type": "image",
+            "source": {
+                "type": "file",
+                "media_type": "image/jpeg",
+                "file_id": "file_123",
+            },
+        }
+        result = transform_content_part(content_part)
+
+        assert result == {
+            "type": "file",
+            "modality": "image",
+            "mime_type": "image/jpeg",
+            "file_id": "file_123",
+        }
+
+    def test_anthropic_document_base64(self):
+        """Test transforming Anthropic document with base64 source"""
+        content_part = {
+            "type": "document",
+            "source": {
+                "type": "base64",
+                "media_type": "application/pdf",
+                "data": "JVBERi0xLjQ=",
+            },
+        }
+        result = transform_content_part(content_part)
+
+        assert result == {
+            "type": "blob",
+            "modality": "document",
+            "mime_type": "application/pdf",
+            "content": "JVBERi0xLjQ=",
+        }
+
+    def test_anthropic_document_url(self):
+        """Test transforming Anthropic document with URL source"""
+        content_part = {
+            "type": "document",
+            "source": {
+                "type": "url",
+                "media_type": "application/pdf",
+                "url": "https://example.com/doc.pdf",
+            },
+        }
+        result = transform_content_part(content_part)
+
+        assert result == {
+            "type": "uri",
+            "modality": "document",
+            "mime_type": "application/pdf",
+            "uri": "https://example.com/doc.pdf",
+        }
+
+    # Google format tests
+    def test_google_inline_data(self):
+        """Test transforming Google inline_data format"""
+        content_part = {
+            "inline_data": {
+                "mime_type": "image/jpeg",
+                "data": "/9j/4AAQSkZJRg==",
+            }
+        }
+        result = transform_content_part(content_part)
+
+        assert result == {
+            "type": "blob",
+            "modality": "image",
+            "mime_type": "image/jpeg",
+            "content": "/9j/4AAQSkZJRg==",
+        }
+
+    def test_google_file_data(self):
+        """Test transforming Google file_data format"""
+        content_part = {
+            "file_data": {
+                "mime_type": "video/mp4",
+                "file_uri": "gs://bucket/video.mp4",
+            }
+        }
+        result = transform_content_part(content_part)
+
+        assert result == {
+            "type": "uri",
+            "modality": "video",
+            "mime_type": "video/mp4",
+            "uri": "gs://bucket/video.mp4",
+        }
+
+    def test_google_inline_data_audio(self):
+        """Test transforming Google inline_data with audio"""
+        content_part = {
+            "inline_data": {
+                "mime_type": "audio/wav",
+                "data": "UklGRiQA",
+            }
+        }
+        result = transform_content_part(content_part)
+
+        assert result == {
+            "type": "blob",
+            "modality": "audio",
+            "mime_type": "audio/wav",
+            "content": "UklGRiQA",
+        }
+
+    # Generic format tests (LangChain style)
+    def test_generic_image_base64(self):
+        """Test transforming generic format with base64"""
+        content_part = {
+            "type": "image",
+            "base64": "/9j/4AAQSkZJRg==",
+            "mime_type": "image/jpeg",
+        }
+        result = transform_content_part(content_part)
+
+        assert result == {
+            "type": "blob",
+            "modality": "image",
+            "mime_type": "image/jpeg",
+            "content": "/9j/4AAQSkZJRg==",
+        }
+
+    def test_generic_audio_url(self):
+        """Test transforming generic format with URL"""
+        content_part = {
+            "type": "audio",
+            "url": "https://example.com/audio.mp3",
+            "mime_type": "audio/mp3",
+        }
+        result = transform_content_part(content_part)
+
+        assert result == {
+            "type": "uri",
+            "modality": "audio",
+            "mime_type": "audio/mp3",
+            "uri": "https://example.com/audio.mp3",
+        }
+
+    def test_generic_file_with_file_id(self):
+        """Test transforming generic format with file_id"""
+        content_part = {
+            "type": "file",
+            "file_id": "file_456",
+            "mime_type": "application/pdf",
+        }
+        result = transform_content_part(content_part)
+
+        assert result == {
+            "type": "file",
+            "modality": "document",
+            "mime_type": "application/pdf",
+            "file_id": "file_456",
+        }
+
+    def test_generic_video_base64(self):
+        """Test transforming generic video format"""
+        content_part = {
+            "type": "video",
+            "base64": "AAAA",
+            "mime_type": "video/mp4",
+        }
+        result = transform_content_part(content_part)
+
+        assert result == {
+            "type": "blob",
+            "modality": "video",
+            "mime_type": "video/mp4",
+            "content": "AAAA",
+        }
+
+    # Edge cases and error handling
+    def test_text_block_returns_none(self):
+        """Test that text blocks return None (not transformed)"""
+        content_part = {"type": "text", "text": "Hello world"}
+        result = transform_content_part(content_part)
+
+        assert result is None
+
+    def test_non_dict_returns_none(self):
+        """Test that non-dict input returns None"""
+        assert transform_content_part("string") is None
+        assert transform_content_part(123) is None
+        assert transform_content_part(None) is None
+        assert transform_content_part([1, 2, 3]) is None
+
+    def test_empty_dict_returns_none(self):
+        """Test that empty dict returns None"""
+        assert transform_content_part({}) is None
+
+    def test_unknown_type_returns_none(self):
+        """Test that unknown type returns None"""
+        content_part = {"type": "unknown", "data": "something"}
+        assert transform_content_part(content_part) is None
+
+    def test_openai_image_url_empty_url_returns_none(self):
+        """Test that image_url with empty URL returns None"""
+        content_part = {"type": "image_url", "image_url": {"url": ""}}
+        assert transform_content_part(content_part) is None
+
+    def test_anthropic_invalid_source_returns_none(self):
+        """Test that Anthropic format with invalid source returns None"""
+        content_part = {"type": "image", "source": "not_a_dict"}
+        assert transform_content_part(content_part) is None
+
+    def test_anthropic_unknown_source_type_returns_none(self):
+        """Test that Anthropic format with unknown source type returns None"""
+        content_part = {
+            "type": "image",
+            "source": {"type": "unknown", "data": "something"},
+        }
+        assert transform_content_part(content_part) is None
+
+    def test_google_inline_data_not_dict_returns_none(self):
+        """Test that Google inline_data with non-dict value returns None"""
+        content_part = {"inline_data": "not_a_dict"}
+        assert transform_content_part(content_part) is None
+
+    def test_google_file_data_not_dict_returns_none(self):
+        """Test that Google file_data with non-dict value returns None"""
+        content_part = {"file_data": "not_a_dict"}
+        assert transform_content_part(content_part) is None
+
+
+class TestTransformMessageContent:
+    def test_string_content_returned_as_is(self):
+        """Test that string content is returned unchanged"""
+        content = "Hello, world!"
+        result = transform_message_content(content)
+
+        assert result == "Hello, world!"
+
+    def test_list_with_transformable_items(self):
+        """Test transforming a list with transformable content parts"""
+        content = [
+            {"type": "text", "text": "What's in this image?"},
+            {
+                "type": "image_url",
+                "image_url": {"url": "data:image/jpeg;base64,/9j/4AAQ"},
+            },
+        ]
+        result = transform_message_content(content)
+
+        assert len(result) == 2
+        # Text block should be unchanged (transform returns None, so original kept)
+        assert result[0] == {"type": "text", "text": "What's in this image?"}
+        # Image should be transformed
+        assert result[1] == {
+            "type": "blob",
+            "modality": "image",
+            "mime_type": "image/jpeg",
+            "content": "/9j/4AAQ",
+        }
+
+    def test_list_with_non_dict_items(self):
+        """Test that non-dict items in list are kept as-is"""
+        content = ["text string", 123, {"type": "text", "text": "hi"}]
+        result = transform_message_content(content)
+
+        assert result == ["text string", 123, {"type": "text", "text": "hi"}]
+
+    def test_tuple_content(self):
+        """Test that tuple content is also handled"""
+        content = (
+            {"type": "text", "text": "Hello"},
+            {
+                "type": "image_url",
+                "image_url": {"url": "https://example.com/img.jpg"},
+            },
+        )
+        result = transform_message_content(content)
+
+        assert len(result) == 2
+        assert result[0] == {"type": "text", "text": "Hello"}
+        assert result[1] == {
+            "type": "uri",
+            "modality": "image",
+            "mime_type": "",
+            "uri": "https://example.com/img.jpg",
+        }
+
+    def test_other_types_returned_as_is(self):
+        """Test that other types are returned unchanged"""
+        assert transform_message_content(123) == 123
+        assert transform_message_content(None) is None
+        assert transform_message_content({"key": "value"}) == {"key": "value"}
+
+    def test_mixed_content_types(self):
+        """Test transforming mixed content with multiple formats"""
+        content = [
+            {"type": "text", "text": "Look at these:"},
+            {
+                "type": "image_url",
+                "image_url": {"url": "data:image/png;base64,iVBORw0"},
+            },
+            {
+                "type": "image",
+                "source": {
+                    "type": "base64",
+                    "media_type": "image/jpeg",
+                    "data": "/9j/4AAQ",
+                },
+            },
+            {"inline_data": {"mime_type": "audio/wav", "data": "UklGRiQA"}},
+        ]
+        result = transform_message_content(content)
+
+        assert len(result) == 4
+        assert result[0] == {"type": "text", "text": "Look at these:"}
+        assert result[1] == {
+            "type": "blob",
+            "modality": "image",
+            "mime_type": "image/png",
+            "content": "iVBORw0",
+        }
+        assert result[2] == {
+            "type": "blob",
+            "modality": "image",
+            "mime_type": "image/jpeg",
+            "content": "/9j/4AAQ",
+        }
+        assert result[3] == {
+            "type": "blob",
+            "modality": "audio",
+            "mime_type": "audio/wav",
+            "content": "UklGRiQA",
+        }
+
+    def test_empty_list(self):
+        """Test that empty list is returned as empty list"""
+        assert transform_message_content([]) == []
diff --git a/tests/test_logs.py b/tests/test_logs.py
index 11c7b8e4d5..386e22658e 100644
--- a/tests/test_logs.py
+++ b/tests/test_logs.py
@@ -471,6 +471,69 @@ def test_logs_with_literal_braces(
         assert "sentry.message.template" not in logs[0]["attributes"]
 
 
+@minimum_python_37
+def test_transport_format(sentry_init, capture_envelopes):
+    sentry_init(enable_logs=True, server_name="test-server", release="1.0.0")
+
+    envelopes = capture_envelopes()
+
+    sentry_sdk.logger.warning("This is a log...")
+
+    sentry_sdk.get_client().flush()
+
+    assert len(envelopes) == 1
+    assert len(envelopes[0].items) == 1
+    item = envelopes[0].items[0]
+
+    assert item.type == "log"
+    assert item.headers == {
+        "type": "log",
+        "item_count": 1,
+        "content_type": "application/vnd.sentry.items.log+json",
+    }
+    assert item.payload.json == {
+        "items": [
+            {
+                "body": "This is a log...",
+                "level": "warn",
+                "timestamp": mock.ANY,
+                "trace_id": mock.ANY,
+                "span_id": mock.ANY,
+                "attributes": {
+                    "sentry.environment": {
+                        "type": "string",
+                        "value": "production",
+                    },
+                    "sentry.release": {
+                        "type": "string",
+                        "value": "1.0.0",
+                    },
+                    "sentry.sdk.name": {
+                        "type": "string",
+                        "value": mock.ANY,
+                    },
+                    "sentry.sdk.version": {
+                        "type": "string",
+                        "value": VERSION,
+                    },
+                    "sentry.severity_number": {
+                        "type": "integer",
+                        "value": 13,
+                    },
+                    "sentry.severity_text": {
+                        "type": "string",
+                        "value": "warn",
+                    },
+                    "server.address": {
+                        "type": "string",
+                        "value": "test-server",
+                    },
+                },
+            }
+        ]
+    }
+
+
 @minimum_python_37
 def test_batcher_drops_logs(sentry_init, monkeypatch):
     sentry_init(enable_logs=True, server_name="test-server", release="1.0.0")
@@ -598,13 +661,71 @@ def test_log_attributes_override_scope_attributes(sentry_init, capture_envelopes
     assert log["attributes"]["temp.attribute"] == "value2"
 
 
+@minimum_python_37
+def test_log_array_attributes(sentry_init, capture_envelopes):
+    """Test homogeneous list and tuple attributes, and fallback for inhomogeneous collections."""
+
+    sentry_init(enable_logs=True)
+
+    envelopes = capture_envelopes()
+
+    with sentry_sdk.new_scope() as scope:
+        scope.set_attribute("string_list", ["value1", "value2"])
+        scope.set_attribute("int_tuple", (3, 2, 1, 4))
+        scope.set_attribute("inhomogeneous_tuple", (3, 2.0, 1, 4))  # type: ignore[arg-type]
+
+        sentry_sdk.logger.warning(
+            "Hello, world!",
+            attributes={
+                "float_list": [3.0, 3.5, 4.2],
+                "bool_tuple": (False, False, True),
+                "inhomogeneous_list": [3.2, True, None],
+            },
+        )
+
+    get_client().flush()
+
+    assert len(envelopes) == 1
+    assert len(envelopes[0].items) == 1
+    item = envelopes[0].items[0]
+    serialized_attributes = item.payload.json["items"][0]["attributes"]
+
+    assert serialized_attributes["string_list"] == {
+        "value": ["value1", "value2"],
+        "type": "string[]",
+    }
+    assert serialized_attributes["int_tuple"] == {
+        "value": [3, 2, 1, 4],
+        "type": "integer[]",
+    }
+    assert serialized_attributes["inhomogeneous_tuple"] == {
+        "value": "(3, 2.0, 1, 4)",
+        "type": "string",
+    }
+
+    assert serialized_attributes["float_list"] == {
+        "value": [3.0, 3.5, 4.2],
+        "type": "double[]",
+    }
+    assert serialized_attributes["bool_tuple"] == {
+        "value": [False, False, True],
+        "type": "boolean[]",
+    }
+    assert serialized_attributes["inhomogeneous_list"] == {
+        "value": "[3.2, True, None]",
+        "type": "string",
+    }
+
+
 @minimum_python_37
 def test_attributes_preserialized_in_before_send(sentry_init, capture_envelopes):
-    """We don't surface references to objects in attributes."""
+    """We don't surface user-held references to objects in attributes."""
 
     def before_send_log(log, _):
         assert isinstance(log["attributes"]["instance"], str)
         assert isinstance(log["attributes"]["dictionary"], str)
+        assert isinstance(log["attributes"]["inhomogeneous_list"], str)
+        assert isinstance(log["attributes"]["inhomogeneous_tuple"], str)
 
         return log
 
@@ -623,6 +744,8 @@ class Cat:
         attributes={
             "instance": instance,
             "dictionary": dictionary,
+            "inhomogeneous_list": [3.2, True, None],
+            "inhomogeneous_tuple": (3, 2.0, 1, 4),
         },
     )
 
@@ -633,3 +756,31 @@ class Cat:
 
     assert isinstance(log["attributes"]["instance"], str)
     assert isinstance(log["attributes"]["dictionary"], str)
+    assert isinstance(log["attributes"]["inhomogeneous_list"], str)
+    assert isinstance(log["attributes"]["inhomogeneous_tuple"], str)
+
+
+@minimum_python_37
+def test_array_attributes_deep_copied_in_before_send(sentry_init, capture_envelopes):
+    """We don't surface user-held references to objects in attributes."""
+
+    strings = ["value1", "value2"]
+    ints = (3, 2, 1, 4)
+
+    def before_send_log(log, _):
+        assert log["attributes"]["string_list"] is not strings
+        assert log["attributes"]["int_tuple"] is not ints
+
+        return log
+
+    sentry_init(enable_logs=True, before_send_log=before_send_log)
+
+    sentry_sdk.logger.warning(
+        "Hello world!",
+        attributes={
+            "string_list": strings,
+            "int_tuple": ints,
+        },
+    )
+
+    get_client().flush()
diff --git a/tests/test_metrics.py b/tests/test_metrics.py
index d64ce748e4..185c1c594d 100644
--- a/tests/test_metrics.py
+++ b/tests/test_metrics.py
@@ -1,6 +1,8 @@
 import json
 import sys
 from typing import List, Any, Mapping
+from unittest import mock
+
 import pytest
 
 import sentry_sdk
@@ -268,6 +270,61 @@ def _before_metric(record, hint):
     assert before_metric_called
 
 
+def test_transport_format(sentry_init, capture_envelopes):
+    sentry_init(server_name="test-server", release="1.0.0")
+
+    envelopes = capture_envelopes()
+
+    sentry_sdk.metrics.count("test.counter", 1)
+
+    sentry_sdk.get_client().flush()
+
+    assert len(envelopes) == 1
+    assert len(envelopes[0].items) == 1
+    item = envelopes[0].items[0]
+
+    assert item.type == "trace_metric"
+    assert item.headers == {
+        "type": "trace_metric",
+        "item_count": 1,
+        "content_type": "application/vnd.sentry.items.trace-metric+json",
+    }
+    assert item.payload.json == {
+        "items": [
+            {
+                "name": "test.counter",
+                "type": "counter",
+                "value": 1,
+                "timestamp": mock.ANY,
+                "trace_id": mock.ANY,
+                "span_id": mock.ANY,
+                "attributes": {
+                    "sentry.environment": {
+                        "type": "string",
+                        "value": "production",
+                    },
+                    "sentry.release": {
+                        "type": "string",
+                        "value": "1.0.0",
+                    },
+                    "sentry.sdk.name": {
+                        "type": "string",
+                        "value": mock.ANY,
+                    },
+                    "sentry.sdk.version": {
+                        "type": "string",
+                        "value": VERSION,
+                    },
+                    "server.address": {
+                        "type": "string",
+                        "value": "test-server",
+                    },
+                },
+            }
+        ]
+    }
+
+
 def test_batcher_drops_metrics(sentry_init, monkeypatch):
     sentry_init()
     client = sentry_sdk.get_client()
@@ -337,12 +394,70 @@ def test_metric_attributes_override_scope_attributes(sentry_init, capture_envelo
     assert metric["attributes"]["temp.attribute"] == "value2"
 
 
+def test_log_array_attributes(sentry_init, capture_envelopes):
+    """Test homogeneous list and tuple attributes, and fallback for inhomogeneous collections."""
+
+    sentry_init()
+
+    envelopes = capture_envelopes()
+
+    with sentry_sdk.new_scope() as scope:
+        scope.set_attribute("string_list.attribute", ["value1", "value2"])
+        scope.set_attribute("int_tuple.attribute", (3, 2, 1, 4))
+        scope.set_attribute("inhomogeneous_tuple.attribute", (3, 2.0, 1, 4))  # type: ignore[arg-type]
+
+        sentry_sdk.metrics.count(
+            "test",
+            1,
+            attributes={
+                "float_list.attribute": [3.0, 3.5, 4.2],
+                "bool_tuple.attribute": (False, False, True),
+                "inhomogeneous_list.attribute": [3.2, True, None],
+            },
+        )
+
+    get_client().flush()
+
+    assert len(envelopes) == 1
+    assert len(envelopes[0].items) == 1
+    item = envelopes[0].items[0]
+    serialized_attributes = item.payload.json["items"][0]["attributes"]
+
+    assert serialized_attributes["string_list.attribute"] == {
+        "value": ["value1", "value2"],
+        "type": "string[]",
+    }
+    assert serialized_attributes["int_tuple.attribute"] == {
+        "value": [3, 2, 1, 4],
+        "type": "integer[]",
+    }
+    assert serialized_attributes["inhomogeneous_tuple.attribute"] == {
+        "value": "(3, 2.0, 1, 4)",
+        "type": "string",
+    }
+
+    assert serialized_attributes["float_list.attribute"] == {
+        "value": [3.0, 3.5, 4.2],
+        "type": "double[]",
+    }
+    assert serialized_attributes["bool_tuple.attribute"] == {
+        "value": [False, False, True],
+        "type": "boolean[]",
+    }
+    assert serialized_attributes["inhomogeneous_list.attribute"] == {
+        "value": "[3.2, True, None]",
+        "type": "string",
+    }
+
+
 def test_attributes_preserialized_in_before_send(sentry_init, capture_envelopes):
-    """We don't surface references to objects in attributes."""
+    """We don't surface user-held references to objects in attributes."""
 
     def before_send_metric(metric, _):
         assert isinstance(metric["attributes"]["instance"], str)
         assert isinstance(metric["attributes"]["dictionary"], str)
+        assert isinstance(metric["attributes"]["inhomogeneous_list"], str)
+        assert isinstance(metric["attributes"]["inhomogeneous_tuple"], str)
 
         return metric
 
@@ -362,6 +477,8 @@ class Cat:
         attributes={
             "instance": instance,
             "dictionary": dictionary,
+            "inhomogeneous_list": [3.2, True, None],
+            "inhomogeneous_tuple": (3, 2.0, 1, 4),
         },
     )
 
@@ -372,3 +489,29 @@ class Cat:
 
     assert isinstance(metric["attributes"]["instance"], str)
     assert isinstance(metric["attributes"]["dictionary"], str)
+
+
+def test_array_attributes_deep_copied_in_before_send(sentry_init, capture_envelopes):
+    """We don't surface user-held references to objects in attributes."""
+
+    strings = ["value1", "value2"]
+    ints = (3, 2, 1, 4)
+
+    def before_send_metric(metric, _):
+        assert metric["attributes"]["string_list"] is not strings
+        assert metric["attributes"]["int_tuple"] is not ints
+
+        return metric
+
+    sentry_init(before_send_metric=before_send_metric)
+
+    sentry_sdk.metrics.count(
+        "test.counter",
+        1,
+        attributes={
+            "string_list": strings,
+            "int_tuple": ints,
+        },
+    )
+
+    get_client().flush()
diff --git a/tests/test_scope.py b/tests/test_scope.py
index 86a0551a44..710ce33849 100644
--- a/tests/test_scope.py
+++ b/tests/test_scope.py
@@ -1021,3 +1021,54 @@ def test_trace_context_without_performance(sentry_init):
     assert trace_context["span_id"] == propagation_context.span_id
     assert trace_context["parent_span_id"] == propagation_context.parent_span_id
     assert "dynamic_sampling_context" in trace_context
+
+
+def test_conversation_id_set_get():
+    """Test that set_conversation_id and get_conversation_id work correctly."""
+    scope = Scope()
+    assert scope.get_conversation_id() is None
+
+    scope.set_conversation_id("test-conv-123")
+    assert scope.get_conversation_id() == "test-conv-123"
+
+
+def test_conversation_id_remove():
+    """Test that remove_conversation_id clears the conversation ID."""
+    scope = Scope()
+    scope.set_conversation_id("test-conv-456")
+    assert scope.get_conversation_id() == "test-conv-456"
+
+    scope.remove_conversation_id()
+    assert scope.get_conversation_id() is None
+
+
+def test_conversation_id_overwrite():
+    """Test that set_conversation_id overwrites existing value."""
+    scope = Scope()
+    scope.set_conversation_id("first-conv")
+    scope.set_conversation_id("second-conv")
+    assert scope.get_conversation_id() == "second-conv"
+
+
+def test_conversation_id_copy():
+    """Test that conversation_id is preserved when scope is copied."""
+    scope1 = Scope()
+    scope1.set_conversation_id("copy-test-conv")
+
+    scope2 = copy.copy(scope1)
+    assert scope2.get_conversation_id() == "copy-test-conv"
+
+    # Modifying copy should not affect original
+    scope2.set_conversation_id("modified-conv")
+    assert scope1.get_conversation_id() == "copy-test-conv"
+    assert scope2.get_conversation_id() == "modified-conv"
+
+
+def test_conversation_id_clear():
+    """Test that conversation_id is cleared when scope.clear() is called."""
+    scope = Scope()
+    scope.set_conversation_id("clear-test-conv")
+    assert scope.get_conversation_id() == "clear-test-conv"
+
+    scope.clear()
+    assert scope.get_conversation_id() is None
diff --git a/tests/test_shadowed_module.py b/tests/test_shadowed_module.py
index efca19746a..10d86f285b 100644
--- a/tests/test_shadowed_module.py
+++ b/tests/test_shadowed_module.py
@@ -26,15 +26,7 @@ def pytest_generate_tests(metafunc):
 
         metafunc.parametrize(
             "integration_submodule_name",
-            # Temporarily skip some integrations
-            submodule_names
-            - {
-                "clickhouse_driver",
-                "litellm",
-                "pure_eval",
-                "ray",
-                "typer",
-            },
+            submodule_names,
         )
 
 
diff --git a/tests/test_transport.py b/tests/test_transport.py
index b5b88e0e2c..8601a4f138 100644
--- a/tests/test_transport.py
+++ b/tests/test_transport.py
@@ -385,6 +385,33 @@ def test_parse_rate_limits(input, expected):
     assert dict(_parse_rate_limits(input, now=NOW)) == expected
 
 
+def test_envelope_too_large_response(capturing_server, make_client):
+    client = make_client()
+
+    capturing_server.respond_with(code=413)
+    client.capture_event({"type": "error"})
+    client.capture_event({"type": "transaction"})
+    client.flush()
+
+    # Error, transaction, and client report payloads
+    assert len(capturing_server.captured) == 3
+    report = parse_json(capturing_server.captured[2].envelope.items[0].get_bytes())
+
+    # Client reports for error, transaction and included span
+    assert len(report["discarded_events"]) == 3
+    assert {"reason": "send_error", "category": "error", "quantity": 1} in report[
+        "discarded_events"
+    ]
+    assert {"reason": "send_error", "category": "span", "quantity": 1} in report[
+        "discarded_events"
+    ]
+    assert {"reason": "send_error", "category": "transaction", "quantity": 1} in report[
+        "discarded_events"
+    ]
+
+    capturing_server.clear_captured()
+
+
 def test_simple_rate_limits(capturing_server, make_client):
     client = make_client()
     capturing_server.respond_with(code=429, headers={"Retry-After": "4"})
diff --git a/tests/tracing/test_misc.py b/tests/tracing/test_misc.py
index e1de847102..8895c98dbc 100644
--- a/tests/tracing/test_misc.py
+++ b/tests/tracing/test_misc.py
@@ -37,6 +37,26 @@ def test_span_trimming(sentry_init, capture_events):
     assert "dropped_spans" not in event
 
 
+def test_span_trimming_produces_client_report(
+    sentry_init, capture_events, capture_record_lost_event_calls
+):
+    sentry_init(traces_sample_rate=1.0, _experiments={"max_spans": 3})
+    events = capture_events()
+    record_lost_event_calls = capture_record_lost_event_calls()
+
+    with start_transaction(name="hi"):
+        for i in range(10):
+            with start_span(op="foo{}".format(i)):
+                pass
+
+    (event,) = events
+
+    assert len(event["spans"]) == 3
+
+    # 7 spans were dropped (10 total - 3 kept = 7 dropped)
+    assert ("buffer_overflow", "span", None, 7) in record_lost_event_calls
+
+
 def test_span_data_scrubbing_and_trimming(sentry_init, capture_events):
     sentry_init(traces_sample_rate=1.0, _experiments={"max_spans": 3})
     events = capture_events()
@@ -585,3 +605,168 @@ def test_update_current_span(sentry_init, capture_events):
         "thread.id": mock.ANY,
         "thread.name": mock.ANY,
     }
+
+
+class TestConversationIdPropagation:
+    """Tests for conversation_id propagation to AI spans."""
+
+    def test_conversation_id_propagates_to_span_with_gen_ai_operation_name(
+        self, sentry_init, capture_events
+    ):
+        """Span with gen_ai.operation.name data should get conversation_id."""
+        sentry_init(traces_sample_rate=1.0)
+        events = capture_events()
+
+        scope = sentry_sdk.get_current_scope()
+        scope.set_conversation_id("conv-op-name-test")
+
+        with sentry_sdk.start_transaction(name="test-tx"):
+            with start_span(op="http.client") as span:
+                span.set_data("gen_ai.operation.name", "chat")
+
+        (event,) = events
+        span_data = event["spans"][0]["data"]
+        assert span_data.get("gen_ai.conversation.id") == "conv-op-name-test"
+
+    def test_conversation_id_propagates_to_span_with_ai_op(
+        self, sentry_init, capture_events
+    ):
+        """Span with ai.* op should get conversation_id."""
+        sentry_init(traces_sample_rate=1.0)
+        events = capture_events()
+
+        scope = sentry_sdk.get_current_scope()
+        scope.set_conversation_id("conv-ai-op-test")
+
+        with sentry_sdk.start_transaction(name="test-tx"):
+            with start_span(op="ai.chat.completions"):
+                pass
+
+        (event,) = events
+        span_data = event["spans"][0]["data"]
+        assert span_data.get("gen_ai.conversation.id") == "conv-ai-op-test"
+
+    def test_conversation_id_propagates_to_span_with_gen_ai_op(
+        self, sentry_init, capture_events
+    ):
+        """Span with gen_ai.* op should get conversation_id."""
+        sentry_init(traces_sample_rate=1.0)
+        events = capture_events()
+
+        scope = sentry_sdk.get_current_scope()
+        scope.set_conversation_id("conv-gen-ai-op-test")
+
+        with sentry_sdk.start_transaction(name="test-tx"):
+            with start_span(op="gen_ai.invoke_agent"):
+                pass
+
+        (event,) = events
+        span_data = event["spans"][0]["data"]
+        assert span_data.get("gen_ai.conversation.id") == "conv-gen-ai-op-test"
+
+    def test_conversation_id_not_propagated_to_non_ai_span(
+        self, sentry_init, capture_events
+    ):
+        """Non-AI span should NOT get conversation_id."""
+        sentry_init(traces_sample_rate=1.0)
+        events = capture_events()
+
+        scope = sentry_sdk.get_current_scope()
+        scope.set_conversation_id("conv-should-not-appear")
+
+        with sentry_sdk.start_transaction(name="test-tx"):
+            with start_span(op="http.client") as span:
+                span.set_data("some.other.data", "value")
+
+        (event,) = events
+        span_data = event["spans"][0]["data"]
+        assert "gen_ai.conversation.id" not in span_data
+
+    def test_conversation_id_not_propagated_when_not_set(
+        self, sentry_init, capture_events
+    ):
+        """AI span should not have conversation_id if not set on scope."""
+        sentry_init(traces_sample_rate=1.0)
+        events = capture_events()
+
+        # Ensure no conversation_id is set
+        scope = sentry_sdk.get_current_scope()
+        scope.remove_conversation_id()
+
+        with sentry_sdk.start_transaction(name="test-tx"):
+            with start_span(op="ai.chat.completions"):
+                pass
+
+        (event,) = events
+        span_data = event["spans"][0]["data"]
+        assert "gen_ai.conversation.id" not in span_data
+
+    def test_conversation_id_not_propagated_to_span_without_op(
+        self, sentry_init, capture_events
+    ):
+        """Span without op and without gen_ai.operation.name should NOT get conversation_id."""
+        sentry_init(traces_sample_rate=1.0)
+        events = capture_events()
+
+        scope = sentry_sdk.get_current_scope()
+        scope.set_conversation_id("conv-no-op-test")
+
+        with sentry_sdk.start_transaction(name="test-tx"):
+            with start_span(name="unnamed-span") as span:
+                span.set_data("regular.data", "value")
+
+        (event,) = events
+        span_data = event["spans"][0]["data"]
+        assert "gen_ai.conversation.id" not in span_data
+
+    def test_conversation_id_propagates_with_gen_ai_operation_name_no_op(
+        self, sentry_init, capture_events
+    ):
+        """Span with gen_ai.operation.name but no op should still get conversation_id."""
+        sentry_init(traces_sample_rate=1.0)
+        events = capture_events()
+
+        scope = sentry_sdk.get_current_scope()
+        scope.set_conversation_id("conv-no-op-but-data-test")
+
+        with sentry_sdk.start_transaction(name="test-tx"):
+            with start_span(name="unnamed-span") as span:
+                span.set_data("gen_ai.operation.name", "embedding")
+
+        (event,) = events
+        span_data = event["spans"][0]["data"]
+        assert span_data.get("gen_ai.conversation.id") == "conv-no-op-but-data-test"
+
+    def test_conversation_id_propagates_to_transaction_with_ai_op(
+        self, sentry_init, capture_events
+    ):
+        """Transaction with ai.* op should get conversation_id."""
+        sentry_init(traces_sample_rate=1.0)
+        events = capture_events()
+
+        scope = sentry_sdk.get_current_scope()
+        scope.set_conversation_id("conv-tx-ai-op-test")
+
+        with sentry_sdk.start_transaction(op="ai.workflow", name="AI Workflow"):
+            pass
+
+        (event,) = events
+        trace_data = event["contexts"]["trace"]["data"]
+        assert trace_data.get("gen_ai.conversation.id") == "conv-tx-ai-op-test"
+
+    def test_conversation_id_not_propagated_to_non_ai_transaction(
+        self, sentry_init, capture_events
+    ):
+        """Non-AI transaction should NOT get conversation_id."""
+        sentry_init(traces_sample_rate=1.0)
+        events = capture_events()
+
+        scope = sentry_sdk.get_current_scope()
+        scope.set_conversation_id("conv-tx-should-not-appear")
+
+        with sentry_sdk.start_transaction(op="http.server", name="HTTP Request"):
+            pass
+
+        (event,) = events
+        trace_data = event["contexts"]["trace"]["data"]
+        assert "gen_ai.conversation.id" not in trace_data
diff --git a/tox.ini b/tox.ini
index 26166555c1..5530002884 100644
--- a/tox.ini
+++ b/tox.ini
@@ -57,80 +57,81 @@ envlist =
 
     # ~~~ MCP ~~~
     {py3.10,py3.12,py3.13}-mcp-v1.15.0
-    {py3.10,py3.12,py3.13}-mcp-v1.18.0
-    {py3.10,py3.12,py3.13}-mcp-v1.21.2
-    {py3.10,py3.12,py3.13}-mcp-v1.24.0
+    {py3.10,py3.12,py3.13}-mcp-v1.19.0
+    {py3.10,py3.12,py3.13}-mcp-v1.23.3
+    {py3.10,py3.12,py3.13}-mcp-v1.26.0
 
     {py3.10,py3.13,py3.14,py3.14t}-fastmcp-v0.1.0
     {py3.10,py3.13,py3.14,py3.14t}-fastmcp-v0.4.1
     {py3.10,py3.13,py3.14,py3.14t}-fastmcp-v1.0
-    {py3.10,py3.12,py3.13}-fastmcp-v2.14.1
+    {py3.10,py3.12,py3.13}-fastmcp-v2.14.4
+    {py3.10,py3.12,py3.13}-fastmcp-v3.0.0b1
 
 
     # ~~~ Agents ~~~
     {py3.10,py3.11,py3.12}-openai_agents-v0.0.19
     {py3.10,py3.12,py3.13}-openai_agents-v0.2.11
     {py3.10,py3.12,py3.13}-openai_agents-v0.4.2
-    {py3.10,py3.13,py3.14,py3.14t}-openai_agents-v0.6.4
+    {py3.10,py3.13,py3.14,py3.14t}-openai_agents-v0.7.0
 
     {py3.10,py3.12,py3.13}-pydantic_ai-v1.0.18
-    {py3.10,py3.12,py3.13}-pydantic_ai-v1.12.0
-    {py3.10,py3.12,py3.13}-pydantic_ai-v1.24.0
-    {py3.10,py3.12,py3.13}-pydantic_ai-v1.36.0
+    {py3.10,py3.12,py3.13}-pydantic_ai-v1.17.0
+    {py3.10,py3.12,py3.13}-pydantic_ai-v1.34.0
+    {py3.10,py3.12,py3.13}-pydantic_ai-v1.51.0
 
 
     # ~~~ AI Workflow ~~~
     {py3.9,py3.11,py3.12}-langchain-base-v0.1.20
     {py3.9,py3.12,py3.13}-langchain-base-v0.3.27
-    {py3.10,py3.13,py3.14}-langchain-base-v1.2.0
+    {py3.10,py3.13,py3.14}-langchain-base-v1.2.7
 
     {py3.9,py3.11,py3.12}-langchain-notiktoken-v0.1.20
     {py3.9,py3.12,py3.13}-langchain-notiktoken-v0.3.27
-    {py3.10,py3.13,py3.14}-langchain-notiktoken-v1.2.0
+    {py3.10,py3.13,py3.14}-langchain-notiktoken-v1.2.7
 
     {py3.9,py3.13,py3.14}-langgraph-v0.6.11
-    {py3.10,py3.12,py3.13}-langgraph-v1.0.5
+    {py3.10,py3.12,py3.13}-langgraph-v1.0.7
 
 
     # ~~~ AI ~~~
     {py3.8,py3.11,py3.12}-anthropic-v0.16.0
     {py3.8,py3.11,py3.12}-anthropic-v0.36.2
     {py3.8,py3.11,py3.12}-anthropic-v0.56.0
-    {py3.9,py3.12,py3.13}-anthropic-v0.75.0
+    {py3.9,py3.13,py3.14,py3.14t}-anthropic-v0.77.0
 
     {py3.9,py3.10,py3.11}-cohere-v5.4.0
     {py3.9,py3.11,py3.12}-cohere-v5.10.0
     {py3.9,py3.11,py3.12}-cohere-v5.15.0
-    {py3.9,py3.11,py3.12}-cohere-v5.20.1
+    {py3.9,py3.11,py3.12}-cohere-v5.20.2
 
     {py3.9,py3.12,py3.13}-google_genai-v1.29.0
-    {py3.9,py3.12,py3.13}-google_genai-v1.38.0
-    {py3.9,py3.13,py3.14,py3.14t}-google_genai-v1.47.0
-    {py3.10,py3.13,py3.14,py3.14t}-google_genai-v1.56.0
+    {py3.9,py3.12,py3.13}-google_genai-v1.40.0
+    {py3.10,py3.13,py3.14,py3.14t}-google_genai-v1.51.0
+    {py3.10,py3.13,py3.14,py3.14t}-google_genai-v1.61.0
 
     {py3.8,py3.10,py3.11}-huggingface_hub-v0.24.7
-    {py3.8,py3.12,py3.13}-huggingface_hub-v0.36.0
-    {py3.9,py3.13,py3.14,py3.14t}-huggingface_hub-v1.2.3
+    {py3.8,py3.12,py3.13}-huggingface_hub-v0.36.1
+    {py3.9,py3.13,py3.14,py3.14t}-huggingface_hub-v1.3.7
 
     {py3.9,py3.12,py3.13}-litellm-v1.77.7
     {py3.9,py3.12,py3.13}-litellm-v1.78.7
     {py3.9,py3.12,py3.13}-litellm-v1.79.3
-    {py3.9,py3.12,py3.13}-litellm-v1.80.10
+    {py3.9,py3.12,py3.13}-litellm-v1.81.6
 
     {py3.8,py3.11,py3.12}-openai-base-v1.0.1
     {py3.8,py3.12,py3.13}-openai-base-v1.109.1
-    {py3.9,py3.13,py3.14,py3.14t}-openai-base-v2.14.0
+    {py3.9,py3.13,py3.14,py3.14t}-openai-base-v2.16.0
 
     {py3.8,py3.11,py3.12}-openai-notiktoken-v1.0.1
     {py3.8,py3.12,py3.13}-openai-notiktoken-v1.109.1
-    {py3.9,py3.13,py3.14,py3.14t}-openai-notiktoken-v2.14.0
+    {py3.9,py3.13,py3.14,py3.14t}-openai-notiktoken-v2.16.0
 
 
     # ~~~ Cloud ~~~
     {py3.6,py3.7}-boto3-v1.12.49
     {py3.6,py3.9,py3.10}-boto3-v1.21.46
     {py3.7,py3.11,py3.12}-boto3-v1.33.13
-    {py3.9,py3.13,py3.14,py3.14t}-boto3-v1.42.13
+    {py3.9,py3.13,py3.14,py3.14t}-boto3-v1.42.39
 
     {py3.6,py3.7,py3.8}-chalice-v1.16.0
     {py3.9,py3.12,py3.13}-chalice-v1.32.0
@@ -146,7 +147,7 @@ envlist =
 
     {py3.6}-pymongo-v3.5.1
     {py3.6,py3.10,py3.11}-pymongo-v3.13.0
-    {py3.9,py3.13,py3.14,py3.14t}-pymongo-v4.15.5
+    {py3.9,py3.13,py3.14,py3.14t}-pymongo-v4.16.0
 
     {py3.6}-redis-v2.10.6
     {py3.6,py3.7,py3.8}-redis-v3.5.3
@@ -158,9 +159,10 @@ envlist =
     {py3.6}-redis_py_cluster_legacy-v1.3.6
     {py3.6,py3.7,py3.8}-redis_py_cluster_legacy-v2.1.3
 
-    {py3.6,py3.8,py3.9}-sqlalchemy-v1.3.24
+    {py3.6,py3.8,py3.9}-sqlalchemy-v1.2.19
     {py3.6,py3.11,py3.12}-sqlalchemy-v1.4.54
-    {py3.7,py3.12,py3.13}-sqlalchemy-v2.0.45
+    {py3.7,py3.12,py3.13}-sqlalchemy-v2.0.46
+    {py3.10,py3.13,py3.14,py3.14t}-sqlalchemy-v2.1.0b1
 
 
     # ~~~ Flags ~~~
@@ -171,25 +173,26 @@ envlist =
     {py3.9,py3.13,py3.14,py3.14t}-openfeature-v0.8.4
 
     {py3.7,py3.13,py3.14}-statsig-v0.55.3
-    {py3.7,py3.13,py3.14}-statsig-v0.66.2
+    {py3.7,py3.13,py3.14}-statsig-v0.67.0
 
     {py3.8,py3.12,py3.13}-unleash-v6.0.1
-    {py3.8,py3.12,py3.13}-unleash-v6.4.1
+    {py3.8,py3.12,py3.13}-unleash-v6.5.1
 
 
     # ~~~ GraphQL ~~~
     {py3.8,py3.10,py3.11}-ariadne-v0.20.1
-    {py3.9,py3.12,py3.13}-ariadne-v0.26.2
+    {py3.10,py3.13,py3.14,py3.14t}-ariadne-v0.27.1
+    {py3.10,py3.13,py3.14,py3.14t}-ariadne-v0.28.0rc2
 
     {py3.6,py3.9,py3.10}-gql-v3.4.1
     {py3.9,py3.12,py3.13}-gql-v4.0.0
-    {py3.9,py3.12,py3.13}-gql-v4.2.0b0
+    {py3.9,py3.13,py3.14,py3.14t}-gql-v4.3.0b0
 
     {py3.6,py3.9,py3.10}-graphene-v3.3
     {py3.8,py3.12,py3.13}-graphene-v3.4.3
 
     {py3.8,py3.10,py3.11}-strawberry-v0.209.8
-    {py3.10,py3.13,py3.14,py3.14t}-strawberry-v0.287.3
+    {py3.10,py3.13,py3.14,py3.14t}-strawberry-v0.291.0
 
 
     # ~~~ Network ~~~
@@ -197,6 +200,7 @@ envlist =
     {py3.7,py3.9,py3.10}-grpc-v1.47.5
     {py3.7,py3.11,py3.12}-grpc-v1.62.3
     {py3.9,py3.13,py3.14}-grpc-v1.76.0
+    {py3.9,py3.13,py3.14}-grpc-v1.78.0rc2
 
     {py3.6,py3.8,py3.9}-httpx-v0.16.1
     {py3.6,py3.9,py3.10}-httpx-v0.20.0
@@ -209,31 +213,31 @@ envlist =
 
     # ~~~ Tasks ~~~
     {py3.7,py3.9,py3.10}-arq-v0.23
-    {py3.8,py3.11,py3.12}-arq-v0.26.3
+    {py3.9,py3.12,py3.13}-arq-v0.27.0
 
     {py3.7}-beam-v2.14.0
-    {py3.10,py3.12,py3.13}-beam-v2.70.0
+    {py3.10,py3.12,py3.13}-beam-v2.71.0
 
     {py3.6,py3.7,py3.8}-celery-v4.4.7
-    {py3.9,py3.12,py3.13}-celery-v5.6.0
+    {py3.9,py3.12,py3.13}-celery-v5.6.2
 
     {py3.6,py3.7}-dramatiq-v1.9.0
-    {py3.10,py3.13,py3.14,py3.14t}-dramatiq-v2.0.0
+    {py3.10,py3.13,py3.14,py3.14t}-dramatiq-v2.0.1
 
     {py3.6,py3.7}-huey-v2.1.3
-    {py3.6,py3.13,py3.14,py3.14t}-huey-v2.5.5
+    {py3.6,py3.13,py3.14,py3.14t}-huey-v2.6.0
 
     {py3.9,py3.10}-ray-v2.7.2
-    {py3.10,py3.12,py3.13}-ray-v2.52.1
+    {py3.10,py3.12,py3.13}-ray-v2.53.0
 
-    {py3.6}-rq-v0.8.2
+    {py3.6}-rq-v0.6.0
     {py3.6,py3.7}-rq-v0.13.0
     {py3.7,py3.11,py3.12}-rq-v1.16.2
     {py3.9,py3.12,py3.13}-rq-v2.6.1
 
     {py3.8,py3.9}-spark-v3.0.3
-    {py3.8,py3.10,py3.11}-spark-v3.5.7
-    {py3.10,py3.13,py3.14}-spark-v4.1.0
+    {py3.8,py3.10,py3.11}-spark-v3.5.8
+    {py3.10,py3.13,py3.14}-spark-v4.1.1
 
 
     # ~~~ Web 1 ~~~
@@ -241,29 +245,29 @@ envlist =
     {py3.6,py3.8,py3.9}-django-v2.2.28
     {py3.6,py3.9,py3.10}-django-v3.2.25
     {py3.8,py3.11,py3.12}-django-v4.2.27
-    {py3.10,py3.13,py3.14,py3.14t}-django-v5.2.9
-    {py3.12,py3.13,py3.14,py3.14t}-django-v6.0
+    {py3.10,py3.13,py3.14,py3.14t}-django-v5.2.10
+    {py3.12,py3.13,py3.14,py3.14t}-django-v6.0.1
 
     {py3.6,py3.7,py3.8}-flask-v1.1.4
     {py3.8,py3.13,py3.14,py3.14t}-flask-v2.3.3
     {py3.9,py3.13,py3.14,py3.14t}-flask-v3.1.2
 
     {py3.6,py3.9,py3.10}-starlette-v0.16.0
-    {py3.7,py3.10,py3.11}-starlette-v0.27.0
-    {py3.8,py3.12,py3.13}-starlette-v0.38.6
-    {py3.10,py3.13,py3.14,py3.14t}-starlette-v0.50.0
+    {py3.7,py3.10,py3.11}-starlette-v0.28.0
+    {py3.8,py3.12,py3.13}-starlette-v0.40.0
+    {py3.10,py3.13,py3.14,py3.14t}-starlette-v0.52.1
 
     {py3.6,py3.9,py3.10}-fastapi-v0.79.1
-    {py3.7,py3.10,py3.11}-fastapi-v0.94.1
-    {py3.8,py3.11,py3.12}-fastapi-v0.109.2
-    {py3.9,py3.13,py3.14,py3.14t}-fastapi-v0.125.0
+    {py3.7,py3.10,py3.11}-fastapi-v0.95.2
+    {py3.8,py3.11,py3.12}-fastapi-v0.111.1
+    {py3.9,py3.13,py3.14,py3.14t}-fastapi-v0.128.0
 
 
     # ~~~ Web 2 ~~~
     {py3.7}-aiohttp-v3.4.4
     {py3.7,py3.8,py3.9}-aiohttp-v3.7.4
     {py3.8,py3.12,py3.13}-aiohttp-v3.10.11
-    {py3.9,py3.13,py3.14,py3.14t}-aiohttp-v3.13.2
+    {py3.9,py3.13,py3.14,py3.14t}-aiohttp-v3.13.3
 
     {py3.6,py3.7}-bottle-v0.12.25
     {py3.8,py3.12,py3.13}-bottle-v0.13.4
@@ -288,7 +292,7 @@ envlist =
     {py3.6}-sanic-v0.8.3
     {py3.6,py3.8,py3.9}-sanic-v20.12.7
     {py3.8,py3.10,py3.11}-sanic-v23.12.2
-    {py3.9,py3.12,py3.13}-sanic-v25.3.0
+    {py3.10,py3.13,py3.14}-sanic-v25.12.0
 
     {py3.8,py3.10,py3.11}-starlite-v1.48.1
     {py3.8,py3.10,py3.11}-starlite-v1.51.16
@@ -307,10 +311,10 @@ envlist =
     {py3.6}-trytond-v4.8.18
     {py3.6,py3.7,py3.8}-trytond-v5.8.16
     {py3.8,py3.10,py3.11}-trytond-v6.8.17
-    {py3.9,py3.12,py3.13}-trytond-v7.8.0
+    {py3.9,py3.12,py3.13}-trytond-v7.8.4
 
     {py3.7,py3.12,py3.13}-typer-v0.15.4
-    {py3.8,py3.13,py3.14,py3.14t}-typer-v0.20.0
+    {py3.9,py3.13,py3.14,py3.14t}-typer-v0.21.1
 
 
 
@@ -380,15 +384,16 @@ deps =
 
     # ~~~ MCP ~~~
     mcp-v1.15.0: mcp==1.15.0
-    mcp-v1.18.0: mcp==1.18.0
-    mcp-v1.21.2: mcp==1.21.2
-    mcp-v1.24.0: mcp==1.24.0
+    mcp-v1.19.0: mcp==1.19.0
+    mcp-v1.23.3: mcp==1.23.3
+    mcp-v1.26.0: mcp==1.26.0
     mcp: pytest-asyncio
 
     fastmcp-v0.1.0: fastmcp==0.1.0
     fastmcp-v0.4.1: fastmcp==0.4.1
     fastmcp-v1.0: fastmcp==1.0
-    fastmcp-v2.14.1: fastmcp==2.14.1
+    fastmcp-v2.14.4: fastmcp==2.14.4
+    fastmcp-v3.0.0b1: fastmcp==3.0.0b1
     fastmcp: pytest-asyncio
 
 
@@ -396,47 +401,47 @@ deps =
     openai_agents-v0.0.19: openai-agents==0.0.19
     openai_agents-v0.2.11: openai-agents==0.2.11
     openai_agents-v0.4.2: openai-agents==0.4.2
-    openai_agents-v0.6.4: openai-agents==0.6.4
+    openai_agents-v0.7.0: openai-agents==0.7.0
     openai_agents: pytest-asyncio
 
     pydantic_ai-v1.0.18: pydantic-ai==1.0.18
-    pydantic_ai-v1.12.0: pydantic-ai==1.12.0
-    pydantic_ai-v1.24.0: pydantic-ai==1.24.0
-    pydantic_ai-v1.36.0: pydantic-ai==1.36.0
+    pydantic_ai-v1.17.0: pydantic-ai==1.17.0
+    pydantic_ai-v1.34.0: pydantic-ai==1.34.0
+    pydantic_ai-v1.51.0: pydantic-ai==1.51.0
     pydantic_ai: pytest-asyncio
 
 
     # ~~~ AI Workflow ~~~
     langchain-base-v0.1.20: langchain==0.1.20
     langchain-base-v0.3.27: langchain==0.3.27
-    langchain-base-v1.2.0: langchain==1.2.0
+    langchain-base-v1.2.7: langchain==1.2.7
     langchain-base: pytest-asyncio
     langchain-base: openai
     langchain-base: tiktoken
     langchain-base: langchain-openai
     langchain-base-v0.3.27: langchain-community
-    langchain-base-v1.2.0: langchain-community
-    langchain-base-v1.2.0: langchain-classic
+    langchain-base-v1.2.7: langchain-community
+    langchain-base-v1.2.7: langchain-classic
 
     langchain-notiktoken-v0.1.20: langchain==0.1.20
     langchain-notiktoken-v0.3.27: langchain==0.3.27
-    langchain-notiktoken-v1.2.0: langchain==1.2.0
+    langchain-notiktoken-v1.2.7: langchain==1.2.7
     langchain-notiktoken: pytest-asyncio
     langchain-notiktoken: openai
     langchain-notiktoken: langchain-openai
     langchain-notiktoken-v0.3.27: langchain-community
-    langchain-notiktoken-v1.2.0: langchain-community
-    langchain-notiktoken-v1.2.0: langchain-classic
+    langchain-notiktoken-v1.2.7: langchain-community
+    langchain-notiktoken-v1.2.7: langchain-classic
 
     langgraph-v0.6.11: langgraph==0.6.11
-    langgraph-v1.0.5: langgraph==1.0.5
+    langgraph-v1.0.7: langgraph==1.0.7
 
 
     # ~~~ AI ~~~
     anthropic-v0.16.0: anthropic==0.16.0
     anthropic-v0.36.2: anthropic==0.36.2
     anthropic-v0.56.0: anthropic==0.56.0
-    anthropic-v0.75.0: anthropic==0.75.0
+    anthropic-v0.77.0: anthropic==0.77.0
     anthropic: pytest-asyncio
     anthropic-v0.16.0: httpx<0.28.0
     anthropic-v0.36.2: httpx<0.28.0
@@ -444,35 +449,35 @@ deps =
     cohere-v5.4.0: cohere==5.4.0
     cohere-v5.10.0: cohere==5.10.0
     cohere-v5.15.0: cohere==5.15.0
-    cohere-v5.20.1: cohere==5.20.1
+    cohere-v5.20.2: cohere==5.20.2
 
     google_genai-v1.29.0: google-genai==1.29.0
-    google_genai-v1.38.0: google-genai==1.38.0
-    google_genai-v1.47.0: google-genai==1.47.0
-    google_genai-v1.56.0: google-genai==1.56.0
+    google_genai-v1.40.0: google-genai==1.40.0
+    google_genai-v1.51.0: google-genai==1.51.0
+    google_genai-v1.61.0: google-genai==1.61.0
     google_genai: pytest-asyncio
 
     huggingface_hub-v0.24.7: huggingface_hub==0.24.7
-    huggingface_hub-v0.36.0: huggingface_hub==0.36.0
-    huggingface_hub-v1.2.3: huggingface_hub==1.2.3
+    huggingface_hub-v0.36.1: huggingface_hub==0.36.1
+    huggingface_hub-v1.3.7: huggingface_hub==1.3.7
     huggingface_hub: responses
     huggingface_hub: pytest-httpx
 
     litellm-v1.77.7: litellm==1.77.7
     litellm-v1.78.7: litellm==1.78.7
     litellm-v1.79.3: litellm==1.79.3
-    litellm-v1.80.10: litellm==1.80.10
+    litellm-v1.81.6: litellm==1.81.6
 
     openai-base-v1.0.1: openai==1.0.1
     openai-base-v1.109.1: openai==1.109.1
-    openai-base-v2.14.0: openai==2.14.0
+    openai-base-v2.16.0: openai==2.16.0
     openai-base: pytest-asyncio
     openai-base: tiktoken
     openai-base-v1.0.1: httpx<0.28
 
     openai-notiktoken-v1.0.1: openai==1.0.1
     openai-notiktoken-v1.109.1: openai==1.109.1
-    openai-notiktoken-v2.14.0: openai==2.14.0
+    openai-notiktoken-v2.16.0: openai==2.16.0
     openai-notiktoken: pytest-asyncio
     openai-notiktoken-v1.0.1: httpx<0.28
 
@@ -481,7 +486,7 @@ deps =
     boto3-v1.12.49: boto3==1.12.49
     boto3-v1.21.46: boto3==1.21.46
     boto3-v1.33.13: boto3==1.33.13
-    boto3-v1.42.13: boto3==1.42.13
+    boto3-v1.42.39: boto3==1.42.39
     {py3.7,py3.8}-boto3: urllib3<2.0.0
 
     chalice-v1.16.0: chalice==1.16.0
@@ -500,7 +505,7 @@ deps =
 
     pymongo-v3.5.1: pymongo==3.5.1
     pymongo-v3.13.0: pymongo==3.13.0
-    pymongo-v4.15.5: pymongo==4.15.5
+    pymongo-v4.16.0: pymongo==4.16.0
     pymongo: mockupdb
 
     redis-v2.10.6: redis==2.10.6
@@ -518,9 +523,10 @@ deps =
     redis_py_cluster_legacy-v1.3.6: redis-py-cluster==1.3.6
     redis_py_cluster_legacy-v2.1.3: redis-py-cluster==2.1.3
 
-    sqlalchemy-v1.3.24: sqlalchemy==1.3.24
+    sqlalchemy-v1.2.19: sqlalchemy==1.2.19
     sqlalchemy-v1.4.54: sqlalchemy==1.4.54
-    sqlalchemy-v2.0.45: sqlalchemy==2.0.45
+    sqlalchemy-v2.0.46: sqlalchemy==2.0.46
+    sqlalchemy-v2.1.0b1: sqlalchemy==2.1.0b1
 
 
     # ~~~ Flags ~~~
@@ -531,23 +537,24 @@ deps =
     openfeature-v0.8.4: openfeature-sdk==0.8.4
 
     statsig-v0.55.3: statsig==0.55.3
-    statsig-v0.66.2: statsig==0.66.2
+    statsig-v0.67.0: statsig==0.67.0
     statsig: typing_extensions
 
     unleash-v6.0.1: UnleashClient==6.0.1
-    unleash-v6.4.1: UnleashClient==6.4.1
+    unleash-v6.5.1: UnleashClient==6.5.1
 
 
     # ~~~ GraphQL ~~~
     ariadne-v0.20.1: ariadne==0.20.1
-    ariadne-v0.26.2: ariadne==0.26.2
+    ariadne-v0.27.1: ariadne==0.27.1
+    ariadne-v0.28.0rc2: ariadne==0.28.0rc2
     ariadne: fastapi
     ariadne: flask
     ariadne: httpx
 
     gql-v3.4.1: gql[all]==3.4.1
     gql-v4.0.0: gql[all]==4.0.0
-    gql-v4.2.0b0: gql[all]==4.2.0b0
+    gql-v4.3.0b0: gql[all]==4.3.0b0
 
     graphene-v3.3: graphene==3.3
     graphene-v3.4.3: graphene==3.4.3
@@ -558,7 +565,7 @@ deps =
     {py3.6}-graphene: aiocontextvars
 
     strawberry-v0.209.8: strawberry-graphql[fastapi,flask]==0.209.8
-    strawberry-v0.287.3: strawberry-graphql[fastapi,flask]==0.287.3
+    strawberry-v0.291.0: strawberry-graphql[fastapi,flask]==0.291.0
     strawberry: httpx
     strawberry-v0.209.8: pydantic<2.11
 
@@ -568,6 +575,7 @@ deps =
     grpc-v1.47.5: grpcio==1.47.5
     grpc-v1.62.3: grpcio==1.62.3
     grpc-v1.76.0: grpcio==1.76.0
+    grpc-v1.78.0rc2: grpcio==1.78.0rc2
     grpc: protobuf
     grpc: mypy-protobuf
     grpc: types-protobuf
@@ -589,44 +597,44 @@ deps =
 
     # ~~~ Tasks ~~~
     arq-v0.23: arq==0.23
-    arq-v0.26.3: arq==0.26.3
+    arq-v0.27.0: arq==0.27.0
     arq: async-timeout
     arq: pytest-asyncio
     arq: fakeredis>=2.2.0,<2.8
     arq-v0.23: pydantic<2
 
     beam-v2.14.0: apache-beam==2.14.0
-    beam-v2.70.0: apache-beam==2.70.0
+    beam-v2.71.0: apache-beam==2.71.0
     beam: dill
 
     celery-v4.4.7: celery==4.4.7
-    celery-v5.6.0: celery==5.6.0
+    celery-v5.6.2: celery==5.6.2
     celery: newrelic<10.17.0
     celery: redis
     {py3.7}-celery: importlib-metadata<5.0
 
     dramatiq-v1.9.0: dramatiq==1.9.0
-    dramatiq-v2.0.0: dramatiq==2.0.0
+    dramatiq-v2.0.1: dramatiq==2.0.1
 
     huey-v2.1.3: huey==2.1.3
-    huey-v2.5.5: huey==2.5.5
+    huey-v2.6.0: huey==2.6.0
 
     ray-v2.7.2: ray==2.7.2
-    ray-v2.52.1: ray==2.52.1
+    ray-v2.53.0: ray==2.53.0
 
-    rq-v0.8.2: rq==0.8.2
+    rq-v0.6.0: rq==0.6.0
     rq-v0.13.0: rq==0.13.0
     rq-v1.16.2: rq==1.16.2
     rq-v2.6.1: rq==2.6.1
     rq: fakeredis<2.28.0
-    rq-v0.8.2: fakeredis<1.0
-    rq-v0.8.2: redis<3.2.2
+    rq-v0.6.0: fakeredis<1.0
+    rq-v0.6.0: redis<3.2.2
     rq-v0.13.0: fakeredis>=1.0,<1.7.4
     {py3.6,py3.7}-rq: fakeredis!=2.26.0
 
     spark-v3.0.3: pyspark==3.0.3
-    spark-v3.5.7: pyspark==3.5.7
-    spark-v4.1.0: pyspark==4.1.0
+    spark-v3.5.8: pyspark==3.5.8
+    spark-v4.1.1: pyspark==4.1.1
 
 
     # ~~~ Web 1 ~~~
@@ -634,8 +642,8 @@ deps =
     django-v2.2.28: django==2.2.28
     django-v3.2.25: django==3.2.25
     django-v4.2.27: django==4.2.27
-    django-v5.2.9: django==5.2.9
-    django-v6.0: django==6.0
+    django-v5.2.10: django==5.2.10
+    django-v6.0.1: django==6.0.1
     django: psycopg2-binary
     django: djangorestframework
     django: pytest-django
@@ -643,13 +651,13 @@ deps =
     django-v2.2.28: channels[daphne]
     django-v3.2.25: channels[daphne]
     django-v4.2.27: channels[daphne]
-    django-v5.2.9: channels[daphne]
-    django-v6.0: channels[daphne]
+    django-v5.2.10: channels[daphne]
+    django-v6.0.1: channels[daphne]
     django-v2.2.28: six
     django-v3.2.25: pytest-asyncio
     django-v4.2.27: pytest-asyncio
-    django-v5.2.9: pytest-asyncio
-    django-v6.0: pytest-asyncio
+    django-v5.2.10: pytest-asyncio
+    django-v6.0.1: pytest-asyncio
     django-v1.11.29: djangorestframework>=3.0,<4.0
     django-v1.11.29: Werkzeug<2.1.0
     django-v2.2.28: djangorestframework>=3.0,<4.0
@@ -669,9 +677,9 @@ deps =
     flask-v1.1.4: markupsafe<2.1.0
 
     starlette-v0.16.0: starlette==0.16.0
-    starlette-v0.27.0: starlette==0.27.0
-    starlette-v0.38.6: starlette==0.38.6
-    starlette-v0.50.0: starlette==0.50.0
+    starlette-v0.28.0: starlette==0.28.0
+    starlette-v0.40.0: starlette==0.40.0
+    starlette-v0.52.1: starlette==0.52.1
     starlette: pytest-asyncio
     starlette: python-multipart
     starlette: requests
@@ -679,21 +687,20 @@ deps =
     starlette: jinja2
     starlette: httpx
     starlette-v0.16.0: httpx<0.28.0
-    starlette-v0.27.0: httpx<0.28.0
+    starlette-v0.28.0: httpx<0.28.0
     {py3.6}-starlette: aiocontextvars
 
     fastapi-v0.79.1: fastapi==0.79.1
-    fastapi-v0.94.1: fastapi==0.94.1
-    fastapi-v0.109.2: fastapi==0.109.2
-    fastapi-v0.125.0: fastapi==0.125.0
+    fastapi-v0.95.2: fastapi==0.95.2
+    fastapi-v0.111.1: fastapi==0.111.1
+    fastapi-v0.128.0: fastapi==0.128.0
     fastapi: httpx
     fastapi: pytest-asyncio
     fastapi: python-multipart
     fastapi: requests
     fastapi: anyio<4
     fastapi-v0.79.1: httpx<0.28.0
-    fastapi-v0.94.1: httpx<0.28.0
-    fastapi-v0.109.2: httpx<0.28.0
+    fastapi-v0.95.2: httpx<0.28.0
     {py3.6}-fastapi: aiocontextvars
 
 
@@ -701,10 +708,10 @@ deps =
     aiohttp-v3.4.4: aiohttp==3.4.4
     aiohttp-v3.7.4: aiohttp==3.7.4
     aiohttp-v3.10.11: aiohttp==3.10.11
-    aiohttp-v3.13.2: aiohttp==3.13.2
+    aiohttp-v3.13.3: aiohttp==3.13.3
     aiohttp: pytest-aiohttp
     aiohttp-v3.10.11: pytest-asyncio
-    aiohttp-v3.13.2: pytest-asyncio
+    aiohttp-v3.13.3: pytest-asyncio
 
     bottle-v0.12.25: bottle==0.12.25
     bottle-v0.13.4: bottle==0.13.4
@@ -747,11 +754,11 @@ deps =
     sanic-v0.8.3: sanic==0.8.3
     sanic-v20.12.7: sanic==20.12.7
     sanic-v23.12.2: sanic==23.12.2
-    sanic-v25.3.0: sanic==25.3.0
+    sanic-v25.12.0: sanic==25.12.0
     sanic: websockets<11.0
     sanic: aiohttp
     sanic-v23.12.2: sanic-testing
-    sanic-v25.3.0: sanic-testing
+    sanic-v25.12.0: sanic-testing
     {py3.6}-sanic: aiocontextvars==0.2.1
     {py3.8}-sanic: tracerite<1.1.2
 
@@ -781,13 +788,13 @@ deps =
     trytond-v4.8.18: trytond==4.8.18
     trytond-v5.8.16: trytond==5.8.16
     trytond-v6.8.17: trytond==6.8.17
-    trytond-v7.8.0: trytond==7.8.0
+    trytond-v7.8.4: trytond==7.8.4
     trytond: werkzeug
     trytond-v4.6.22: werkzeug<1.0
     trytond-v4.8.18: werkzeug<1.0
 
     typer-v0.15.4: typer==0.15.4
-    typer-v0.20.0: typer==0.20.0
+    typer-v0.21.1: typer==0.21.1
 
 
 
@@ -928,3 +935,4 @@ commands =
     ruff check tests sentry_sdk
     ruff format --check tests sentry_sdk
     mypy sentry_sdk
+    python scripts/find_raise_from_none.py