diff --git a/scripts/update-demo.py b/scripts/update-demo.py
index 4d2ad30..55386fb 100644
--- a/scripts/update-demo.py
+++ b/scripts/update-demo.py
@@ -7,7 +7,11 @@
 import typer
 from cookiecutter.utils import work_in
 
+from util import is_ancestor
+from util import get_current_branch
+from util import get_current_commit
 from util import get_demo_name
+from util import get_last_cruft_update_commit
 from util import git
 from util import FolderOption
 from util import REPO_FOLDER
@@ -24,26 +28,60 @@ def update_demo(
 ) -> None:
     """Runs precommit in a generated project and matches the template to the results."""
     try:
-        develop_branch: str = os.getenv("COOKIECUTTER_ROBUST_PYTHON_DEVELOP_BRANCH", "develop")
         demo_name: str = get_demo_name(add_rust_extension=add_rust_extension)
         demo_path: Path = demos_cache_folder / demo_name
+
+        current_branch: str = get_current_branch()
+        current_commit: str = get_current_commit()
+
+        _validate_is_feature_branch(branch=current_branch)
+
+        last_update_commit: str = _get_last_demo_develop_cruft_update(demo_path=demo_path)
+
+        if not is_ancestor(last_update_commit, current_commit):
+            raise ValueError(
+                f"The last update commit '{last_update_commit}' is not an ancestor of the current commit "
+                f"'{current_commit}'."
+            )
+
         typer.secho(f"Updating demo project at {demo_path=}.", fg="yellow")
         with work_in(demo_path):
-            require_clean_and_up_to_date_repo()
-            git("checkout", develop_branch)
+            if current_branch != "develop":
+                git("checkout", "-b", current_branch)
+
             cruft.update(
                 project_dir=demo_path,
                 template_path=REPO_FOLDER,
                 extra_context={"project_name": demo_name, "add_rust_extension": add_rust_extension},
             )
             git("add", ".")
-            git("commit", "-m", "chore: update demo to the latest cookiecutter-robust-python", "--no-verify")
-            git("push")
+            git("commit", "-m", f"chore: {last_update_commit} -> {current_commit}", "--no-verify")
+            git("push", "-u", "origin", current_branch)
 
     except Exception as error:
         typer.secho(f"error: {error}", fg="red")
         sys.exit(1)
 
 
+def _get_last_demo_develop_cruft_update(demo_path: Path) -> str:
+    """Gets the last cruft update commit for the demo project's develop branch."""
+    _prep_demo_develop(demo_path=demo_path)
+    last_update_commit: str = get_last_cruft_update_commit(demo_path=demo_path)
+    return last_update_commit
+
+
+def _prep_demo_develop(demo_path: Path) -> None:
+    """Checks out the demo development branch and validates it is up to date."""
+    with work_in(demo_path):
+        require_clean_and_up_to_date_repo()
+        git("checkout", "develop")
+
+
+def _validate_is_feature_branch(branch: str) -> None:
+    """Validates that the cookiecutter has a feature branch checked out."""
+    if not branch.startswith("feature/"):
+        raise ValueError(f"Received branch '{branch}' is not a feature branch.")
+
+
 if __name__ == '__main__':
     cli()
diff --git a/scripts/util.py b/scripts/util.py
index 5ce7147..ac30f5f 100644
--- a/scripts/util.py
+++ b/scripts/util.py
@@ -1,4 +1,5 @@
 """Module containing utility functions used throughout cookiecutter_robust_python scripts."""
+import json
 import os
 import shutil
 import stat
@@ -16,7 +17,9 @@
 
 import cruft
 import typer
+
 from cookiecutter.utils import work_in
+from cruft._commands.utils.cruft import get_cruft_file
 from dotenv import load_dotenv
 from typer.models import OptionInfo
 
@@ -42,7 +45,6 @@ def _load_env() -> None:
 # Load environment variables at module import time
 _load_env()
 
-
 FolderOption: partial[OptionInfo] = partial(
     typer.Option, dir_okay=True, file_okay=False, resolve_path=True, path_type=Path
 )
@@ -106,7 +108,38 @@ def is_branch_synced_with_remote(branch: str) -> bool:
 
 def is_ancestor(ancestor: str, descendent: str) -> bool:
     """Checks if the branch is synced with its remote."""
-    return git("merge-base", "--is-ancestor", ancestor, descendent).returncode == 0
+    try:
+        git("merge-base", "--is-ancestor", ancestor, descendent)
+        return True
+    except subprocess.CalledProcessError:
+        return False
+
+
+def get_current_branch() -> str:
+    """Returns the current branch name."""
+    return git("branch", "--show-current").stdout.strip()
+
+
+def get_current_commit() -> str:
+    """Returns the current commit reference."""
+    return git("rev-parse", "HEAD").stdout.strip()
+
+
+def get_last_cruft_update_commit(demo_path: Path) -> str:
+    """Returns the commit id for the last time cruft update was ran."""
+    existing_cruft_config: dict[str, Any] = _read_cruft_file(demo_path)
+    last_cookiecutter_commit: Optional[str] = existing_cruft_config.get("commit", None)
+    if last_cookiecutter_commit is None:
+        raise ValueError("Could not find last commit id used to generate demo.")
+    return last_cookiecutter_commit
+
+
+def _read_cruft_file(project_path: Path) -> dict[str, Any]:
+    """Reads the cruft file for the project path provided and returns the results."""
+    cruft_path: Path = get_cruft_file(project_dir_path=project_path)
+    cruft_text: str = cruft_path.read_text()
+    cruft_config: dict[str, Any] = json.loads(cruft_text)
+    return cruft_config
 
 
 @contextmanager