diff --git a/surfsense_backend/app/agents/new_chat/tools/notion/delete_page.py b/surfsense_backend/app/agents/new_chat/tools/notion/delete_page.py
index f1a65a14a..91c31519a 100644
--- a/surfsense_backend/app/agents/new_chat/tools/notion/delete_page.py
+++ b/surfsense_backend/app/agents/new_chat/tools/notion/delete_page.py
@@ -95,8 +95,19 @@ def create_delete_notion_page_tool(
                         "message": error_msg,
                     }
 
+            account = context.get("account", {})
+            if account.get("auth_expired"):
+                logger.warning(
+                    "Notion account %s has expired authentication",
+                    account.get("id"),
+                )
+                return {
+                    "status": "auth_error",
+                    "message": "The Notion account for this page needs re-authentication. Please re-authenticate in your connector settings.",
+                }
+
             page_id = context.get("page_id")
-            connector_id_from_context = context.get("account", {}).get("id")
+            connector_id_from_context = account.get("id")
             document_id = context.get("document_id")
 
             logger.info(
diff --git a/surfsense_backend/app/agents/new_chat/tools/notion/update_page.py b/surfsense_backend/app/agents/new_chat/tools/notion/update_page.py
index 306cd4b68..965ffc278 100644
--- a/surfsense_backend/app/agents/new_chat/tools/notion/update_page.py
+++ b/surfsense_backend/app/agents/new_chat/tools/notion/update_page.py
@@ -110,6 +110,17 @@ def create_update_notion_page_tool(
                         "message": error_msg,
                     }
 
+            account = context.get("account", {})
+            if account.get("auth_expired"):
+                logger.warning(
+                    "Notion account %s has expired authentication",
+                    account.get("id"),
+                )
+                return {
+                    "status": "auth_error",
+                    "message": "The Notion account for this page needs re-authentication. Please re-authenticate in your connector settings.",
+                }
+
             page_id = context.get("page_id")
             document_id = context.get("document_id")
             connector_id_from_context = context.get("account", {}).get("id")
diff --git a/surfsense_backend/app/services/notion/tool_metadata_service.py b/surfsense_backend/app/services/notion/tool_metadata_service.py
index ca882c5c0..694f8cf6f 100644
--- a/surfsense_backend/app/services/notion/tool_metadata_service.py
+++ b/surfsense_backend/app/services/notion/tool_metadata_service.py
@@ -167,8 +167,26 @@ class NotionToolMetadataService:
         if not page_id:
             return {"error": "Page ID not found in document metadata"}
 
+        acc_dict = account.to_dict()
+        auth_expired = await self._check_account_health(connector.id)
+        acc_dict["auth_expired"] = auth_expired
+        if auth_expired:
+            try:
+                db_connector = connector
+                if not db_connector.config.get("auth_expired"):
+                    db_connector.config = {**db_connector.config, "auth_expired": True}
+                    flag_modified(db_connector, "config")
+                    await self._db_session.commit()
+                    await self._db_session.refresh(db_connector)
+            except Exception:
+                logger.warning(
+                    "Failed to persist auth_expired for connector %s",
+                    connector.id,
+                    exc_info=True,
+                )
+
         return {
-            "account": account.to_dict(),
+            "account": acc_dict,
             "page_id": page_id,
             "current_title": document.title,
             "document_id": document.id,