diff --git a/enterprise/storage/database.py b/enterprise/storage/database.py
index 57e0c833a7..ec06550e03 100644
--- a/enterprise/storage/database.py
+++ b/enterprise/storage/database.py
@@ -21,16 +21,21 @@ POOL_SIZE = int(os.environ.get('DB_POOL_SIZE', '25'))
 MAX_OVERFLOW = int(os.environ.get('DB_MAX_OVERFLOW', '10'))
 POOL_RECYCLE = int(os.environ.get('DB_POOL_RECYCLE', '1800'))
 
+# Initialize Cloud SQL Connector once at module level for GCP environments.
+_connector = None
+
 
 def _get_db_engine():
     if GCP_DB_INSTANCE:  # GCP environments
 
         def get_db_connection():
+            global _connector
             from google.cloud.sql.connector import Connector
 
-            connector = Connector()
+            if not _connector:
+                _connector = Connector()
             instance_string = f'{GCP_PROJECT}:{GCP_REGION}:{GCP_DB_INSTANCE}'
-            return connector.connect(
+            return _connector.connect(
                 instance_string, 'pg8000', user=DB_USER, password=DB_PASS, db=DB_NAME
             )
 
diff --git a/openhands/app_server/app_conversation/app_conversation_router.py b/openhands/app_server/app_conversation/app_conversation_router.py
index 532602dbca..f5d2b996c7 100644
--- a/openhands/app_server/app_conversation/app_conversation_router.py
+++ b/openhands/app_server/app_conversation/app_conversation_router.py
@@ -210,11 +210,17 @@ async def start_app_conversation(
     set_db_session_keep_open(request.state, True)
     set_httpx_client_keep_open(request.state, True)
 
-    """Start an app conversation start task and return it."""
-    async_iter = app_conversation_service.start_app_conversation(start_request)
-    result = await anext(async_iter)
-    asyncio.create_task(_consume_remaining(async_iter, db_session, httpx_client))
-    return result
+    try:
+        """Start an app conversation start task and return it."""
+        async_iter = app_conversation_service.start_app_conversation(start_request)
+        result = await anext(async_iter)
+        asyncio.create_task(_consume_remaining(async_iter, db_session, httpx_client))
+        return result
+    except Exception:
+        await db_session.close()
+        await httpx_client.aclose()
+        raise
+
 
 
 @router.post('/stream-start')
diff --git a/openhands/app_server/event_callback/webhook_router.py b/openhands/app_server/event_callback/webhook_router.py
index 37ae9d89b2..62dd7bec16 100644
--- a/openhands/app_server/event_callback/webhook_router.py
+++ b/openhands/app_server/event_callback/webhook_router.py
@@ -21,12 +21,10 @@ from openhands.app_server.app_conversation.app_conversation_models import (
 )
 from openhands.app_server.config import (
     depends_app_conversation_info_service,
-    depends_db_session,
     depends_event_service,
     depends_jwt_service,
     depends_sandbox_service,
     get_event_callback_service,
-    get_global_config,
 )
 from openhands.app_server.errors import AuthError
 from openhands.app_server.event.event_service import EventService
@@ -54,8 +52,6 @@ sandbox_service_dependency = depends_sandbox_service()
 event_service_dependency = depends_event_service()
 app_conversation_info_service_dependency = depends_app_conversation_info_service()
 jwt_dependency = depends_jwt_service()
-config = get_global_config()
-db_session_dependency = depends_db_session()
 _logger = logging.getLogger(__name__)
 
 
diff --git a/openhands/app_server/services/db_session_injector.py b/openhands/app_server/services/db_session_injector.py
index b7fd404f00..737e1ff879 100644
--- a/openhands/app_server/services/db_session_injector.py
+++ b/openhands/app_server/services/db_session_injector.py
@@ -4,7 +4,7 @@ import asyncio
 import logging
 import os
 from pathlib import Path
-from typing import AsyncGenerator
+from typing import Any, AsyncGenerator
 
 import asyncpg
 from fastapi import Request
@@ -44,6 +44,7 @@ class DbSessionInjector(BaseModel, Injector[async_sessionmaker]):
     _async_engine: AsyncEngine | None = PrivateAttr(default=None)
     _session_maker: sessionmaker | None = PrivateAttr(default=None)
     _async_session_maker: async_sessionmaker | None = PrivateAttr(default=None)
+    _gcp_connector: Any = PrivateAttr(default=None)
 
     @model_validator(mode='after')
     def fill_empty_fields(self):
@@ -67,14 +68,18 @@ class DbSessionInjector(BaseModel, Injector[async_sessionmaker]):
         return self
 
     def _create_gcp_db_connection(self):
-        # Lazy import because lib does not import if user does not have posgres installed
-        from google.cloud.sql.connector import Connector
+        gcp_connector = self._gcp_connector
+        if gcp_connector is None:
+            # Lazy import because lib does not import if user does not have posgres installed
+            from google.cloud.sql.connector import Connector
+
+            gcp_connector = Connector()
+            self._gcp_connector = gcp_connector
 
-        connector = Connector()
         instance_string = f'{self.gcp_project}:{self.gcp_region}:{self.gcp_db_instance}'
         password = self.password
         assert password is not None
-        return connector.connect(
+        return gcp_connector.connect(
             instance_string,
             'pg8000',
             user=self.user,
@@ -83,21 +88,25 @@ class DbSessionInjector(BaseModel, Injector[async_sessionmaker]):
         )
 
     async def _create_async_gcp_db_connection(self):
-        # Lazy import because lib does not import if user does not have posgres installed
-        from google.cloud.sql.connector import Connector
+        gcp_connector = self._gcp_connector
+        if gcp_connector is None:
+            # Lazy import because lib does not import if user does not have posgres installed
+            from google.cloud.sql.connector import Connector
 
-        loop = asyncio.get_running_loop()
-        async with Connector(loop=loop) as connector:
-            password = self.password
-            assert password is not None
-            conn = await connector.connect_async(
-                f'{self.gcp_project}:{self.gcp_region}:{self.gcp_db_instance}',
-                'asyncpg',
-                user=self.user,
-                password=password.get_secret_value(),
-                db=self.name,
-            )
-            return conn
+            loop = asyncio.get_running_loop()
+            gcp_connector = Connector(loop=loop)
+            self._gcp_connector = gcp_connector
+
+        password = self.password
+        assert password is not None
+        conn = await gcp_connector.connect_async(
+            f'{self.gcp_project}:{self.gcp_region}:{self.gcp_db_instance}',
+            'asyncpg',
+            user=self.user,
+            password=password.get_secret_value(),
+            db=self.name,
+        )
+        return conn
 
     def _create_gcp_engine(self):
         engine = create_engine(