diff --git a/pyproject.toml b/pyproject.toml
index 4a924eb1f..e6841571b 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -28,7 +28,7 @@ dependencies = [
     "auth0-python>=4.7.1",
     "python-dotenv>=1.0.0",
     # Configuration and Utils
-    "click>=8.0.1",
+    "click>=8.0.1,<8.2.0",
     "appdirs>=1.4.4",
     "jsonref>=1.1.0",
     "json-repair>=0.25.2",
diff --git a/tests/cli/test_click_compatibility.py b/tests/cli/test_click_compatibility.py
index fbdfe8b04..43f3a6c93 100644
--- a/tests/cli/test_click_compatibility.py
+++ b/tests/cli/test_click_compatibility.py
@@ -4,45 +4,72 @@ import tempfile
 
 import pytest
 
+# Constants for test configuration
+VENV_PATH = "venv"
+TEST_COMMAND = "version"
+EXPECTED_OUTPUT = "crewai version"
+IMPORT_SUCCESS_MESSAGE = "CLI import successful"
 
-def test_crewai_cli_works_with_compatible_click_version():
-    """Test that crewAI CLI works with Click version compatible with zenml."""
+
+def run_subprocess(*args, **kwargs):
+    """Helper function to run subprocess with error handling."""
+    try:
+        result = subprocess.run(*args, **kwargs)
+        result.check_returncode()
+        return result
+    except subprocess.CalledProcessError as e:
+        pytest.fail(f"Subprocess failed with exit code {e.returncode}: {e.stderr if hasattr(e, 'stderr') else ''}")
+
+
+@pytest.mark.parametrize("click_version", ["8.0.1", "8.1.3", "8.1.4"])
+def test_crewai_cli_works_with_compatible_click_version(click_version):
+    """
+    Verifies crewAI CLI works with multiple Click versions.
+    
+    Dependencies:
+        - Click versions compatible with zenml constraints
+    
+    Parameters:
+        click_version: The version of Click to test with
+    """
     # Create a temporary virtual environment
     with tempfile.TemporaryDirectory() as temp_dir:
+        venv_path = f"{temp_dir}/{VENV_PATH}"
+        
         # Create a new virtual environment
-        subprocess.run(
-            [sys.executable, "-m", "venv", f"{temp_dir}/venv"],
+        run_subprocess(
+            [sys.executable, "-m", "venv", venv_path],
             check=True,
         )
         
-        # Install Click 8.1.3 (compatible with zenml's constraints)
-        subprocess.run(
-            [f"{temp_dir}/venv/bin/pip", "install", "click==8.1.3"],
+        # Install specific Click version (compatible with zenml's constraints)
+        run_subprocess(
+            [f"{venv_path}/bin/pip", "install", f"click=={click_version}"],
             check=True,
         )
         
         # Install crewai in development mode
-        subprocess.run(
-            [f"{temp_dir}/venv/bin/pip", "install", "-e", "."],
+        run_subprocess(
+            [f"{venv_path}/bin/pip", "install", "-e", "."],
             check=True,
         )
         
         # Verify that the crewai CLI can be imported and run
-        result = subprocess.run(
-            [f"{temp_dir}/venv/bin/python", "-c", "from crewai.cli.cli import crewai; print('CLI import successful')"],
+        result = run_subprocess(
+            [f"{venv_path}/bin/python", "-c", "from crewai.cli.cli import crewai; print('CLI import successful')"],
             capture_output=True,
             text=True,
         )
         
-        assert result.returncode == 0
-        assert "CLI import successful" in result.stdout
+        assert result.returncode == 0, f"CLI import failed with output: {result.stderr}"
+        assert IMPORT_SUCCESS_MESSAGE in result.stdout, "Failed to import CLI module"
         
         # Test running a basic CLI command
-        result = subprocess.run(
-            [f"{temp_dir}/venv/bin/python", "-m", "crewai.cli.cli", "version"],
+        result = run_subprocess(
+            [f"{venv_path}/bin/python", "-m", "crewai.cli.cli", TEST_COMMAND],
             capture_output=True,
             text=True,
         )
         
-        assert result.returncode == 0
-        assert "crewai version" in result.stdout
+        assert result.returncode == 0, f"CLI command failed with output: {result.stderr}"
+        assert EXPECTED_OUTPUT in result.stdout, f"Expected output '{EXPECTED_OUTPUT}' not found in command result"