diff --git a/backend/app/api/v1/auth.py b/backend/app/api/v1/auth.py
index 5e3bbb5..a2f806b 100644
--- a/backend/app/api/v1/auth.py
+++ b/backend/app/api/v1/auth.py
@@ -162,6 +162,9 @@ async def login(
 ):
     """Login user and return access tokens"""
     
+    logger.info(f"==================================================")
+    logger.info(f"=== LOGIN ENDPOINT REACHED ===")
+    logger.info(f"==================================================")
     logger.info(f"=== LOGIN DEBUG ===")
     logger.info(f"Login attempt for email: {user_data.email}")
     logger.info(f"Current UTC time: {datetime.utcnow().isoformat()}")
@@ -170,6 +173,21 @@ async def login(
     logger.info(f"Settings check - ADMIN_EMAIL: {settings.ADMIN_EMAIL}")
     logger.info(f"Settings check - BCRYPT_ROUNDS: {settings.BCRYPT_ROUNDS}")
     
+    # DEBUG: Check Redis connection
+    try:
+        logger.info("Testing Redis connection...")
+        import redis.asyncio as redis
+        redis_url = settings.REDIS_URL
+        logger.info(f"Redis URL: {redis_url}")
+        redis_client = redis.from_url(redis_url)
+        test_start = datetime.utcnow()
+        await redis_client.ping()
+        test_end = datetime.utcnow()
+        logger.info(f"Redis connection test successful. Time: {(test_end - test_start).total_seconds()} seconds")
+        await redis_client.close()
+    except Exception as e:
+        logger.error(f"Redis connection test failed: {e}")
+    
     # DEBUG: Check database connection with timeout
     try:
         logger.info("Testing database connection...")
diff --git a/backend/app/middleware/debugging.py b/backend/app/middleware/debugging.py
index ca2dd29..6a29a41 100644
--- a/backend/app/middleware/debugging.py
+++ b/backend/app/middleware/debugging.py
@@ -74,6 +74,13 @@ class DebuggingMiddleware(BaseHTTPMiddleware):
         # Add timeout detection
         try:
             logger.info(f"=== START PROCESSING REQUEST === {request_id} at {datetime.utcnow().isoformat()}")
+            logger.info(f"Request path: {request.url.path}")
+            logger.info(f"Request method: {request.method}")
+            
+            # Check if this is the login endpoint
+            if request.url.path == "/api-internal/v1/auth/login" and request.method == "POST":
+                logger.info(f"=== LOGIN REQUEST DETECTED === {request_id}")
+                
             response = await call_next(request)
             logger.info(f"=== REQUEST COMPLETED === {request_id} at {datetime.utcnow().isoformat()}")