diff --git a/surfsense_backend/app/agents/new_chat/checkpointer.py b/surfsense_backend/app/agents/new_chat/checkpointer.py
index 637b2926f..04ecfbdea 100644
--- a/surfsense_backend/app/agents/new_chat/checkpointer.py
+++ b/surfsense_backend/app/agents/new_chat/checkpointer.py
@@ -3,15 +3,25 @@ PostgreSQL-based checkpointer for LangGraph agents.
 
 This module provides a persistent checkpointer using AsyncPostgresSaver
 that stores conversation state in the PostgreSQL database.
+
+Uses a connection pool (psycopg_pool.AsyncConnectionPool) to handle
+connection lifecycle, health checks, and automatic reconnection,
+preventing 'the connection is closed' errors in long-running deployments.
 """
 
+import logging
+
 from langgraph.checkpoint.postgres.aio import AsyncPostgresSaver
+from psycopg.rows import dict_row
+from psycopg_pool import AsyncConnectionPool
 
 from app.config import config
 
+logger = logging.getLogger(__name__)
+
 # Global checkpointer instance (initialized lazily)
 _checkpointer: AsyncPostgresSaver | None = None
-_checkpointer_context = None  # Store the context manager for cleanup
+_connection_pool: AsyncConnectionPool | None = None
 _checkpointer_initialized: bool = False
 
 
@@ -38,26 +48,65 @@ def get_postgres_connection_string() -> str:
     return db_url
 
 
+async def _create_checkpointer() -> AsyncPostgresSaver:
+    """
+    Create a new AsyncPostgresSaver backed by a connection pool.
+
+    The connection pool automatically handles:
+    - Connection health checks before use
+    - Reconnection when connections die (idle timeout, DB restart, etc.)
+    - Connection lifecycle management (max_lifetime, max_idle)
+    """
+    global _connection_pool
+
+    conn_string = get_postgres_connection_string()
+
+    _connection_pool = AsyncConnectionPool(
+        conninfo=conn_string,
+        min_size=2,
+        max_size=10,
+        # Connections are recycled after 30 minutes to avoid stale connections
+        max_lifetime=1800,
+        # Idle connections are closed after 5 minutes
+        max_idle=300,
+        open=False,
+        # Connection kwargs required by AsyncPostgresSaver:
+        # - autocommit: required for .setup() to commit checkpoint tables
+        # - prepare_threshold: disable prepared statements for compatibility
+        # - row_factory: checkpointer accesses rows as dicts (row["column"])
+        kwargs={
+            "autocommit": True,
+            "prepare_threshold": 0,
+            "row_factory": dict_row,
+        },
+    )
+    await _connection_pool.open(wait=True)
+
+    checkpointer = AsyncPostgresSaver(conn=_connection_pool)
+    logger.info("[Checkpointer] Created AsyncPostgresSaver with connection pool")
+    return checkpointer
+
+
 async def get_checkpointer() -> AsyncPostgresSaver:
     """
     Get or create the global AsyncPostgresSaver instance.
 
     This function:
-    1. Creates the checkpointer if it doesn't exist
+    1. Creates the checkpointer with a connection pool if it doesn't exist
     2. Sets up the required database tables on first call
     3. Returns the cached instance on subsequent calls
 
+    The underlying connection pool handles reconnection automatically,
+    so a stale/closed connection will not cause OperationalError.
+
     Returns:
         AsyncPostgresSaver: The configured checkpointer instance
     """
-    global _checkpointer, _checkpointer_context, _checkpointer_initialized
+    global _checkpointer, _checkpointer_initialized
 
     if _checkpointer is None:
-        conn_string = get_postgres_connection_string()
-        # from_conn_string returns an async context manager
-        # We need to enter the context to get the actual checkpointer
-        _checkpointer_context = AsyncPostgresSaver.from_conn_string(conn_string)
-        _checkpointer = await _checkpointer_context.__aenter__()
+        _checkpointer = await _create_checkpointer()
+        _checkpointer_initialized = False
 
     # Setup tables on first call (idempotent)
     if not _checkpointer_initialized:
@@ -75,20 +124,21 @@ async def setup_checkpointer_tables() -> None:
     tables exist before any agent calls.
     """
     await get_checkpointer()
-    print("[Checkpointer] PostgreSQL checkpoint tables ready")
+    logger.info("[Checkpointer] PostgreSQL checkpoint tables ready")
 
 
 async def close_checkpointer() -> None:
     """
-    Close the checkpointer connection.
+    Close the checkpointer connection pool.
 
     This should be called during application shutdown.
     """
-    global _checkpointer, _checkpointer_context, _checkpointer_initialized
+    global _checkpointer, _connection_pool, _checkpointer_initialized
 
-    if _checkpointer_context is not None:
-        await _checkpointer_context.__aexit__(None, None, None)
-        _checkpointer = None
-        _checkpointer_context = None
-        _checkpointer_initialized = False
-        print("[Checkpointer] PostgreSQL connection closed")
+    if _connection_pool is not None:
+        await _connection_pool.close()
+        logger.info("[Checkpointer] PostgreSQL connection pool closed")
+
+    _checkpointer = None
+    _connection_pool = None
+    _checkpointer_initialized = False