diff --git a/guardrails/cli/configure.py b/guardrails/cli/configure.py
index 60ffeb63c..2a7354892 100644
--- a/guardrails/cli/configure.py
+++ b/guardrails/cli/configure.py
@@ -66,8 +66,18 @@ def configure(
 ):
     if clear_token is True:
         token = DEFAULT_TOKEN
+    try:
+        save_configuration_file(token, enable_metrics)
+        logger.info("Configuration saved.")
+
+        if not token:
+            logger.info("No token provided. Skipping authentication.")
+    except Exception as e:
+        logger.error("An unexpected error occured!")
+        logger.error(e)
+        sys.exit(1)
 
-    # Authenticate with the Hub if token is not empty
+        # Authenticate with the Hub if token is not empty
     if token != "" and token is not None:
         logger.info("Validating credentials...")
         try:
@@ -85,16 +95,6 @@ def configure(
             """
             logger.log(level=LEVELS.get("SUCCESS", 25), msg=success_message)
         except AuthenticationError as e:
-            logger.warn(e)
+            logger.error(e)
             # We do not want to exit the program if the user fails to authenticate
             # instead, save the token and other configuration options
-    try:
-        save_configuration_file(token, enable_metrics)
-        logger.info("Configuration saved.")
-
-        if not token:
-            logger.info("No token provided. Skipping authentication.")
-    except Exception as e:
-        logger.error("An unexpected error occured!")
-        logger.error(e)
-        sys.exit(1)
diff --git a/guardrails/cli/server/hub_client.py b/guardrails/cli/server/hub_client.py
index f14bd6a3d..d29bf2781 100644
--- a/guardrails/cli/server/hub_client.py
+++ b/guardrails/cli/server/hub_client.py
@@ -10,12 +10,14 @@
 from guardrails.cli.logger import logger
 from guardrails.cli.server.module_manifest import ModuleManifest
 
-TOKEN_EXPIRED_MESSAGE = (
-    "Your token has expired. Please run `guardrails configure` to update your token."
-)
-TOKEN_INVALID_MESSAGE = (
-    "Your token is invalid. Please run `guardrails configure` to update your token."
-)
+FIND_NEW_TOKEN = "You can find a new token at https://hub.guardrailsai.com/tokens"
+
+TOKEN_EXPIRED_MESSAGE = f"""Your token has expired. Please run `guardrails configure`\
+to update your token.
+{FIND_NEW_TOKEN}"""
+TOKEN_INVALID_MESSAGE = f"""Your token is invalid. Please run `guardrails configure`\
+to update your token.
+{FIND_NEW_TOKEN}"""
 
 validator_hub_service = "https://so4sg4q4pb.execute-api.us-east-1.amazonaws.com"
 validator_manifest_endpoint = Template(
@@ -27,6 +29,14 @@ class AuthenticationError(Exception):
     pass
 
 
+class ExpiredTokenError(Exception):
+    pass
+
+
+class InvalidTokenError(Exception):
+    pass
+
+
 class HttpError(Exception):
     status: int
     message: str
@@ -80,9 +90,9 @@ def get_jwt_token(creds: Credentials) -> Optional[str]:
         except JWTDecodeError as e:
             # if the error message includes "Expired", then the token is expired
             if "Expired" in str(e):
-                raise Exception(TOKEN_EXPIRED_MESSAGE)
+                raise ExpiredTokenError(TOKEN_EXPIRED_MESSAGE)
             else:
-                raise Exception(TOKEN_INVALID_MESSAGE)
+                raise InvalidTokenError(TOKEN_INVALID_MESSAGE)
     return token
 
 
@@ -105,6 +115,9 @@ def get_validator_manifest(module_name: str):
     except HttpError:
         logger.error(f"Failed to install hub://{module_name}")
         sys.exit(1)
+    except (ExpiredTokenError, InvalidTokenError) as e:
+        logger.error(AuthenticationError(e))
+        sys.exit(1)
     except Exception as e:
         logger.error("An unexpected error occurred!", e)
         sys.exit(1)
@@ -122,6 +135,8 @@ def get_auth():
     except HttpError as http_error:
         logger.error(http_error)
         raise AuthenticationError("Failed to authenticate!")
+    except (ExpiredTokenError, InvalidTokenError) as e:
+        raise AuthenticationError(e)
     except Exception as e:
         logger.error("An unexpected error occurred!", e)
         raise AuthenticationError("Failed to authenticate!")
diff --git a/tests/unit_tests/cli/test_configure.py b/tests/unit_tests/cli/test_configure.py
index 5fd6dae9d..dd1e2620a 100644
--- a/tests/unit_tests/cli/test_configure.py
+++ b/tests/unit_tests/cli/test_configure.py
@@ -26,7 +26,7 @@ def test_configure(mocker, token, no_metrics):
     configure(token, no_metrics)
 
     assert mock_logger_info.call_count == 2
-    expected_calls = [call("Validating credentials..."), call("Configuration saved.")]
+    expected_calls = [call("Configuration saved."), call("Validating credentials...")]
     mock_logger_info.assert_has_calls(expected_calls)
 
     mock_save_configuration_file.assert_called_once_with(token, no_metrics)