diff --git a/cron/update_questions.py b/cron/update_questions.py
index 6c9dd5c7..8c05222b 100644
--- a/cron/update_questions.py
+++ b/cron/update_questions.py
@@ -3,37 +3,25 @@
 import leetcode
 import leetcode.auth
 from datetime import datetime
+from leetcode.rest import ApiException
 
-LEETCODE_SESSION_TOKEN = os.environ.get("LEETCODE_SESSION_TOKEN")
 
-questions_file = os.getcwd() + "/src/data/questions.json"
+def create_leetcode_api():
+    LEETCODE_SESSION_TOKEN = os.environ.get("LEETCODE_SESSION_TOKEN")
+    csrf_token = leetcode.auth.get_csrf_cookie(LEETCODE_SESSION_TOKEN)
 
-print("=== Reading questions file ===")
+    configuration = leetcode.Configuration()
 
-try:
-    with open(questions_file, "r") as file:
-        questions = json.load(file)
-except Exception as e:
-    print(e)
-    exit()
+    configuration.api_key["x-csrftoken"] = csrf_token
+    configuration.api_key["csrftoken"] = csrf_token
+    configuration.api_key["LEETCODE_SESSION"] = LEETCODE_SESSION_TOKEN
+    configuration.api_key["Referer"] = "https://leetcode.com"
+    configuration.debug = False
 
-print("=== Updating question metadata ===")
+    return leetcode.DefaultApi(leetcode.ApiClient(configuration))
 
-startTime = datetime.now()
 
-csrf_token = leetcode.auth.get_csrf_cookie(LEETCODE_SESSION_TOKEN)
-
-configuration = leetcode.Configuration()
-
-configuration.api_key["x-csrftoken"] = csrf_token
-configuration.api_key["csrftoken"] = csrf_token
-configuration.api_key["LEETCODE_SESSION"] = LEETCODE_SESSION_TOKEN
-configuration.api_key["Referer"] = "https://leetcode.com"
-configuration.debug = False
-
-api_instance = leetcode.DefaultApi(leetcode.ApiClient(configuration))
-
-for question in questions["data"]:
+def get_question_metadata(api, title_slug):
     graphql_request = leetcode.GraphqlQuery(
         query='''query questionData($titleSlug: String!) {
             question(titleSlug: $titleSlug) {
@@ -45,45 +33,102 @@
         }
         ''',
         variables=leetcode.GraphqlQueryGetQuestionDetailVariables(
-            title_slug=question["slug"])
+            title_slug=title_slug)
     )
 
-    response = api_instance.graphql_post(body=graphql_request).to_dict()
+    try:
+        response = api.graphql_post(body=graphql_request)
+    except ApiException as e:
+        print(
+            f'Exception occurred when contacting the Leetcode GraphQL API: ${e}')
+        exit()
 
-    leetcode_title = response["data"]["question"]["title"]
-    leetcode_difficulty = response["data"]["question"]["difficulty"]
-    leetcode_companyTags = json.loads(
-        response["data"]["question"]["company_tag_stats"])
-    leetcode_premium = response["data"]["question"]["is_paid_only"]
+    return response
 
-    # Retrieve companies who have asked this question within 0-1 year
-    leetcode_companies = leetcode_companyTags["1"] + leetcode_companyTags["2"]
 
+def construct_company_tag_list(company_tags_json, sections):
     companies = []
 
-    for leetcode_company in leetcode_companies:
-        companies.append({
-            "name": leetcode_company["name"],
-            "slug": leetcode_company["slug"],
-            "frequency": leetcode_company["timesEncountered"]
-        })
+    for section in sections:
+        for company in company_tags_json[section]:
+            companies.append({
+                "name": company["name"],
+                "slug": company["slug"],
+                "frequency": company["timesEncountered"]
+            })
+
+    return sorted(companies, key=lambda d: d['frequency'], reverse=True)
+
 
-    companies = sorted(companies, key = lambda d: d['frequency'], reverse=True)
+def update_question_metadata(question, title, difficulty, companies, is_premium):
+    print(f"🔄 Updating question metadata for {title}")
 
-    question["title"] = leetcode_title
-    question["difficulty"] = leetcode_difficulty
+    question["title"] = title
+    question["difficulty"] = difficulty
     question["companies"] = companies
-    question["premium"] = leetcode_premium
+    question["premium"] = is_premium
+
+
+def read_questions(file_name):
+    print(f"💾 Loading {file_name}")
+
+    try:
+        with open(file_name, "r") as file:
+            questions = json.load(file)
+            print(f"✅ Finished loading {file_name}")
+            return questions
+    except Exception as e:
+        print(
+            f"❌ Exception occurred when reading {file_name}: {e}")
+        exit()
+
+
+def write_questions(file_name, questions):
+    print(f"💾 Updating {file_name}")
+
+    try:
+        with open(file_name, "w") as file:
+            questions["updated"] = str(datetime.now().isoformat())
+            json.dump(questions, file, indent=2)
+            print(f"✅ Finished updating {file_name}")
+    except Exception as e:
+        print(
+            f"❌ Exception occurred when writing {file_name}: {e}")
+        exit()
+
+
+def main(file_name):
+    api = create_leetcode_api()
+    questions = read_questions(file_name)
+
+    for question in questions["data"]:
+        title_slug = question["slug"]
+
+        response = get_question_metadata(api, title_slug)
+
+        question_title = response.data.question.title
+        question_difficulty = response.data.question.difficulty
+        question_company_tags = json.loads(
+            response.data.question.company_tag_stats)
+        question_is_premium = response.data.question.is_paid_only
+
+        # Retrieve companies who have asked this question within the following two
+        # company_tag_stat sections:
+        #   1. 0-6 months
+        #   2. 6 months to 1 year
+        companies = construct_company_tag_list(
+            question_company_tags, ["1", "2"])
+
+        update_question_metadata(question, question_title, question_difficulty,
+                                 companies, question_is_premium)
+
+    write_questions(file_name, questions)
+
 
-print("=== Finished checking all questions ===")
+if __name__ == "__main__":
+    file_name = os.getcwd() + "/src/data/questions.json"
+    startTime = datetime.now()
 
-try:
-    with open(questions_file, "w") as file:
-        questions["updated"] = str(datetime.now().isoformat())
-        json.dump(questions, file, indent=2)
-except Exception as e:
-    print(e)
-    exit()
+    main(file_name)
 
-print("=== Wrote questions file ===")
-print(f'=== Script took: {datetime.now() - startTime} seconds ===')
+    print(f"⏱️  Data updated in {datetime.now() - startTime} seconds")