diff --git a/surfsense_backend/app/agents/new_chat/tools/mcp_tool.py b/surfsense_backend/app/agents/new_chat/tools/mcp_tool.py
index 9743d049d..cf3e51166 100644
--- a/surfsense_backend/app/agents/new_chat/tools/mcp_tool.py
+++ b/surfsense_backend/app/agents/new_chat/tools/mcp_tool.py
@@ -377,6 +377,118 @@ async def _load_http_mcp_tools(
     return tools
 
 
+_TOKEN_REFRESH_BUFFER_SECONDS = 300  # refresh 5 min before expiry
+
+
+async def _maybe_refresh_mcp_oauth_token(
+    session: AsyncSession,
+    connector: "SearchSourceConnector",
+    cfg: dict[str, Any],
+    server_config: dict[str, Any],
+) -> dict[str, Any]:
+    """Refresh the access token for an MCP OAuth connector if it is about to expire.
+
+    Returns the (possibly updated) ``server_config``.
+    """
+    from datetime import UTC, datetime, timedelta
+
+    mcp_oauth = cfg.get("mcp_oauth", {})
+    expires_at_str = mcp_oauth.get("expires_at")
+    if not expires_at_str:
+        return server_config
+
+    try:
+        expires_at = datetime.fromisoformat(expires_at_str)
+        if expires_at.tzinfo is None:
+            from datetime import timezone
+            expires_at = expires_at.replace(tzinfo=timezone.utc)
+
+        if datetime.now(UTC) < expires_at - timedelta(seconds=_TOKEN_REFRESH_BUFFER_SECONDS):
+            return server_config
+    except (ValueError, TypeError):
+        return server_config
+
+    refresh_token = mcp_oauth.get("refresh_token")
+    if not refresh_token:
+        logger.warning(
+            "MCP connector %s token expired but no refresh_token available",
+            connector.id,
+        )
+        return server_config
+
+    try:
+        from app.config import config as app_config
+        from app.services.mcp_oauth.discovery import refresh_access_token
+        from app.utils.oauth_security import TokenEncryption
+
+        enc = TokenEncryption(app_config.SECRET_KEY)
+        decrypted_refresh = enc.decrypt_token(refresh_token)
+        decrypted_secret = (
+            enc.decrypt_token(mcp_oauth["client_secret"])
+            if mcp_oauth.get("client_secret")
+            else ""
+        )
+
+        token_json = await refresh_access_token(
+            token_endpoint=mcp_oauth["token_endpoint"],
+            refresh_token=decrypted_refresh,
+            client_id=mcp_oauth["client_id"],
+            client_secret=decrypted_secret,
+        )
+
+        new_access = token_json.get("access_token")
+        if not new_access:
+            logger.warning(
+                "MCP connector %s token refresh returned no access_token",
+                connector.id,
+            )
+            return server_config
+
+        new_expires_at = None
+        if token_json.get("expires_in"):
+            new_expires_at = datetime.now(UTC) + timedelta(
+                seconds=int(token_json["expires_in"])
+            )
+
+        updated_oauth = dict(mcp_oauth)
+        updated_oauth["access_token"] = enc.encrypt_token(new_access)
+        if token_json.get("refresh_token"):
+            updated_oauth["refresh_token"] = enc.encrypt_token(
+                token_json["refresh_token"]
+            )
+        updated_oauth["expires_at"] = (
+            new_expires_at.isoformat() if new_expires_at else None
+        )
+
+        updated_server_config = dict(server_config)
+        updated_server_config["headers"] = {
+            **server_config.get("headers", {}),
+            "Authorization": f"Bearer {new_access}",
+        }
+
+        from sqlalchemy.orm.attributes import flag_modified
+
+        connector.config = {
+            **cfg,
+            "server_config": updated_server_config,
+            "mcp_oauth": updated_oauth,
+        }
+        flag_modified(connector, "config")
+        await session.commit()
+        await session.refresh(connector)
+
+        logger.info("Refreshed MCP OAuth token for connector %s", connector.id)
+        return updated_server_config
+
+    except Exception:
+        logger.warning(
+            "Failed to refresh MCP OAuth token for connector %s",
+            connector.id,
+            exc_info=True,
+        )
+        return server_config
+
+
 def invalidate_mcp_tools_cache(search_space_id: int | None = None) -> None:
     """Invalidate cached MCP tools.
 
@@ -429,9 +541,9 @@ async def load_mcp_tools(
         tools: list[StructuredTool] = []
         for connector in result.scalars():
             try:
-                config = connector.config or {}
-                server_config = config.get("server_config", {})
-                trusted_tools = config.get("trusted_tools", [])
+                cfg = connector.config or {}
+                server_config = cfg.get("server_config", {})
+                trusted_tools = cfg.get("trusted_tools", [])
 
                 if not server_config or not isinstance(server_config, dict):
                     logger.warning(
@@ -439,6 +551,12 @@ async def load_mcp_tools(
                     )
                     continue
 
+                # Refresh OAuth token for MCP OAuth connectors before connecting
+                if cfg.get("mcp_oauth"):
+                    server_config = await _maybe_refresh_mcp_oauth_token(
+                        session, connector, cfg, server_config,
+                    )
+
                 transport = server_config.get("transport", "stdio")
 
                 if transport in ("streamable-http", "http", "sse"):