diff --git a/surfsense_backend/app/agents/new_chat/tools/google_drive/create_file.py b/surfsense_backend/app/agents/new_chat/tools/google_drive/create_file.py
index b8490c12b..0dd683f7e 100644
--- a/surfsense_backend/app/agents/new_chat/tools/google_drive/create_file.py
+++ b/surfsense_backend/app/agents/new_chat/tools/google_drive/create_file.py
@@ -48,8 +48,11 @@ def create_create_google_drive_file_tool(
             - web_view_link: URL to open the file (if success)
             - message: Result message
 
-            IMPORTANT: If status is "rejected", the user explicitly declined the action.
-            Respond with a brief acknowledgment and do NOT retry or suggest alternatives.
+            IMPORTANT:
+            - If status is "rejected", the user explicitly declined the action.
+              Respond with a brief acknowledgment and do NOT retry or suggest alternatives.
+            - If status is "insufficient_permissions", the connector lacks the required OAuth scope.
+              Inform the user they need to re-authenticate and do NOT retry the action.
 
         Examples:
             - "Create a Google Doc called 'Meeting Notes'"
diff --git a/surfsense_backend/app/agents/new_chat/tools/google_drive/trash_file.py b/surfsense_backend/app/agents/new_chat/tools/google_drive/trash_file.py
index 660f518c6..45fa52610 100644
--- a/surfsense_backend/app/agents/new_chat/tools/google_drive/trash_file.py
+++ b/surfsense_backend/app/agents/new_chat/tools/google_drive/trash_file.py
@@ -40,6 +40,8 @@ def create_trash_google_drive_file_tool(
               acknowledgment and do NOT retry or suggest alternatives.
             - If status is "not_found", relay the exact message to the user and ask them
               to verify the file name or check if it has been indexed.
+            - If status is "insufficient_permissions", the connector lacks the required OAuth scope.
+              Inform the user they need to re-authenticate and do NOT retry the action.
 
         Examples:
             - "Delete the 'Meeting Notes' file from Google Drive"