diff --git a/backend/python_service/db.py b/backend/python_service/db.py
index 26f5a71..36feba9 100644
--- a/backend/python_service/db.py
+++ b/backend/python_service/db.py
@@ -3,6 +3,7 @@ Database connection module for Python service
 Uses asyncpg for async PostgreSQL connections
 """
 import os
+import asyncio
 import asyncpg
 from typing import Optional
 from dotenv import load_dotenv
@@ -12,9 +13,12 @@ load_dotenv()
 # Database connection pool
 _pool: Optional[asyncpg.Pool] = None
 
+# Connection timeout in seconds (reduced from default 60s to fail faster)
+CONNECTION_TIMEOUT = 10
+
 
 async def get_pool() -> asyncpg.Pool:
-    """Get or create database connection pool"""
+    """Get or create database connection pool with timeout"""
     global _pool
     
     if _pool is None:
@@ -47,12 +51,29 @@ async def get_pool() -> asyncpg.Pool:
                 '  - OR DATABASE_URL'
             )
         
-        _pool = await asyncpg.create_pool(
-            **config,
-            min_size=5,
-            max_size=20,
-            command_timeout=60
-        )
+        # Create pool with timeout to prevent hanging
+        # Use min_size=1 to speed up initial connection (pool will grow as needed)
+        try:
+            _pool = await asyncio.wait_for(
+                asyncpg.create_pool(
+                    **config,
+                    min_size=1,  # Start with 1 connection, pool grows as needed
+                    max_size=20,
+                    command_timeout=60,
+                    timeout=CONNECTION_TIMEOUT  # Connection timeout per connection
+                ),
+                timeout=CONNECTION_TIMEOUT  # Overall timeout for pool creation
+            )
+        except asyncio.TimeoutError:
+            raise ConnectionError(
+                f'Database connection timeout after {CONNECTION_TIMEOUT}s. '
+                f'Check if database is reachable at {config.get("host", "unknown")}:{config.get("port", "unknown")}'
+            )
+        except Exception as e:
+            raise ConnectionError(
+                f'Failed to create database connection pool: {str(e)}. '
+                f'Check database configuration and network connectivity.'
+            )
     
     return _pool
 
diff --git a/backend/python_service/main.py b/backend/python_service/main.py
index 43b46d7..ee08f16 100644
--- a/backend/python_service/main.py
+++ b/backend/python_service/main.py
@@ -47,7 +47,18 @@ class OptionsFlowResponse(BaseModel):
 @app.on_event("startup")
 async def startup():
     """Initialize database pool on startup"""
-    await get_pool()
+    try:
+        logger.info("Initializing database connection pool...")
+        pool = await get_pool()
+        # Test the connection with a quick query
+        async with pool.acquire() as conn:
+            await conn.fetchval("SELECT 1")
+        logger.info("✅ Database connection pool initialized successfully")
+    except Exception as e:
+        logger.error(f"⚠️ Failed to initialize database pool on startup: {str(e)}")
+        logger.warning("Service will start but database operations may fail. Connection will be retried on first request.")
+        # Don't raise - allow service to start and retry on first request
+        # This makes the service more resilient to temporary DB issues
 
 
 @app.on_event("shutdown")