diff --git a/Testing/Functional/SmokeTests/smoke_test.py b/Testing/Functional/SmokeTests/smoke_test.py
index 7d9abaaa..0474b141 100644
--- a/Testing/Functional/SmokeTests/smoke_test.py
+++ b/Testing/Functional/SmokeTests/smoke_test.py
@@ -37,8 +37,57 @@ def test_cli(self, subjectemail):
 
         directories = [d for d in os.listdir() if os.path.isdir(d) and d.startswith(prefix)]
         directories.sort(key=lambda d: os.path.getctime(d), reverse=True)
-        print(directories)
-        print(directories[0])
+
+        output_path = os.path.join(cwd, directories[0])
+        individual_reports_path = f"{output_path}/IndividualReports"
+        print(individual_reports_path)
+
+        def check_output_contents(output_path):
+            try:
+                entries = os.listdir(output_path)
+                print(entries)
+                for entry in entries:
+                    child_path = os.path.join(output_path, entry)
+
+                    # Directory case
+                    if os.path.isdir(child_path):
+                        assert os.path.isdir(child_path)
+                        check_output_contents(child_path)
+                    
+                    # File case
+                    elif os.path.isfile(child_path):
+                        assert os.path.isfile(child_path)
+                    
+                    # Neither a directory or file (symlink, etc.)
+                    else:
+                        assert False
+            except FileNotFoundError:
+                assert False, f"The directory {output_path} does not exist"
+            except Exception as e:
+                assert False, f"An error occurred, {e}"
+        
+        check_output_contents(output_path)
+
+        #assert "BaselineReports.html" in entries and os.path.isfile(f"{output_path}/BaselineReports.html")
+        #assert "IndividualReports" in entries and os.path.isdir(individual_reports_path)
+        #assert "ProviderSettingsExport.json" in entries and os.path.isfile(f"{output_path}/ProviderSettingsExport.json")
+        #assert "TestResults.json" in entries and os.path.isfile(f"{output_path}/TestResults.json")
+#
+        #assert "CalendarReport.html" in os.listdir(individual_reports_path)
+        #assert "ChatReport.html" in os.listdir(individual_reports_path)
+        #assert "ClassroomReport.html" in os.listdir(individual_reports_path)
+        #assert "CommoncontrolsReport.html" in os.listdir(individual_reports_path)
+        #assert "DriveReport.html" in os.listdir(individual_reports_path)
+        #assert "GmailReport.html" in os.listdir(individual_reports_path)
+        #assert "GroupsReport.html" in os.listdir(individual_reports_path)
+        #assert "MeetReport.html" in os.listdir(individual_reports_path)
+        #assert "RulesReport.html" in os.listdir(individual_reports_path)
+        #assert "SitesReport.html" in os.listdir(individual_reports_path)
+
+
+
+
+
 
 
 #def create_venv(env):