diff --git a/src/backend/base/langflow/services/auth/utils.py b/src/backend/base/langflow/services/auth/utils.py
index f62d3ce4f..ebea58e7a 100644
--- a/src/backend/base/langflow/services/auth/utils.py
+++ b/src/backend/base/langflow/services/auth/utils.py
@@ -1,14 +1,13 @@
+import warnings
 from datetime import datetime, timedelta, timezone
 from typing import Annotated, Coroutine, Optional, Union
 from uuid import UUID
-import warnings
 
 from cryptography.fernet import Fernet
 from fastapi import Depends, HTTPException, Security, status
 from fastapi.security import APIKeyHeader, APIKeyQuery, OAuth2PasswordBearer
-
-
 from jose import JWTError, jwt
+from loguru import logger
 from sqlmodel import Session
 from starlette.websockets import WebSocket
 
@@ -92,44 +91,58 @@ async def get_current_user_by_jwt(
 ) -> User:
     settings_service = get_settings_service()
 
-    credentials_exception = HTTPException(
-        status_code=status.HTTP_401_UNAUTHORIZED,
-        detail="Could not validate credentials",
-        headers={"WWW-Authenticate": "Bearer"},
-    )
-
     if isinstance(token, Coroutine):
         token = await token
 
-    if settings_service.auth_settings.SECRET_KEY.get_secret_value() is None:
-        raise credentials_exception
+    secret_key = settings_service.auth_settings.SECRET_KEY.get_secret_value()
+    if secret_key is None:
+        logger.error("Secret key is not set in settings.")
+        raise HTTPException(
+            status_code=status.HTTP_401_UNAUTHORIZED,
+            # Careful not to leak sensitive information
+            detail="Authentication failure: Verify authentication settings.",
+            headers={"WWW-Authenticate": "Bearer"},
+        )
 
     try:
-        # Ignore warning about datetime.utcnow
         with warnings.catch_warnings():
             warnings.simplefilter("ignore")
-
-            payload = jwt.decode(
-                token,
-                settings_service.auth_settings.SECRET_KEY.get_secret_value(),
-                algorithms=[settings_service.auth_settings.ALGORITHM],
-            )
-        user_id: UUID = payload.get("sub")  # type: ignore
-        token_type: str = payload.get("type")  # type: ignore
+            payload = jwt.decode(token, secret_key, algorithms=[settings_service.auth_settings.ALGORITHM])
+        user_id: UUID = payload.get("sub")
+        token_type: str = payload.get("type")
         if expires := payload.get("exp", None):
             expires_datetime = datetime.fromtimestamp(expires, timezone.utc)
-            # TypeError: can't compare offset-naive and offset-aware datetimes
             if datetime.now(timezone.utc) > expires_datetime:
-                raise credentials_exception
+                logger.info("Token expired for user ID: %s", user_id)
+                raise HTTPException(
+                    status_code=status.HTTP_401_UNAUTHORIZED,
+                    detail="Token has expired.",
+                    headers={"WWW-Authenticate": "Bearer"},
+                )
 
         if user_id is None or token_type:
-            raise credentials_exception
+            logger.info("Invalid token payload: %s", payload)
+            raise HTTPException(
+                status_code=status.HTTP_401_UNAUTHORIZED,
+                detail="Invalid token details.",
+                headers={"WWW-Authenticate": "Bearer"},
+            )
     except JWTError as e:
-        raise credentials_exception from e
+        logger.error("JWT decoding error: %s", str(e))
+        raise HTTPException(
+            status_code=status.HTTP_401_UNAUTHORIZED,
+            detail="Could not validate credentials",
+            headers={"WWW-Authenticate": "Bearer"},
+        ) from e
 
-    user = get_user_by_id(db, user_id)  # type: ignore
+    user = get_user_by_id(db, user_id)
     if user is None or not user.is_active:
-        raise credentials_exception
+        logger.info("User not found or inactive: %s", user_id)
+        raise HTTPException(
+            status_code=status.HTTP_401_UNAUTHORIZED,
+            detail="User not found or is inactive.",
+            headers={"WWW-Authenticate": "Bearer"},
+        )
     return user
 
 
diff --git a/tests/test_user.py b/tests/test_user.py
index 5f894e801..759ce6aaf 100644
--- a/tests/test_user.py
+++ b/tests/test_user.py
@@ -1,6 +1,7 @@
 from datetime import datetime
 
 import pytest
+
 from langflow.services.auth.utils import create_super_user, get_password_hash
 from langflow.services.database.models.user import UserUpdate
 from langflow.services.database.models.user.model import User
@@ -95,7 +96,7 @@ def test_data_consistency_after_update(client, active_user, logged_in_headers, s
     # Fetch the updated user from the database
     response = client.get("/api/v1/users/whoami", headers=logged_in_headers)
     assert response.status_code == 401, response.json()
-    assert response.json()["detail"] == "Could not validate credentials"
+    assert response.json()["detail"] == "User not found or is inactive."
 
 
 def test_data_consistency_after_delete(client, test_user, super_user_headers):