diff --git a/surfsense_backend/app/tasks/connector_indexers/clickup_indexer.py b/surfsense_backend/app/tasks/connector_indexers/clickup_indexer.py
index 7b40a4b22..91763129f 100644
--- a/surfsense_backend/app/tasks/connector_indexers/clickup_indexer.py
+++ b/surfsense_backend/app/tasks/connector_indexers/clickup_indexer.py
@@ -437,10 +437,15 @@ async def index_clickup_tasks(
                 try:
                     document.status = DocumentStatus.failed(str(e))
                     document.updated_at = get_current_timestamp()
+                    # Commit now so the failed status survives a later rollback or
+                    # crash; otherwise the doc stays stuck in pending/processing.
+                    await session.commit()
                 except Exception as status_error:
                     logger.error(
                         f"Failed to update document status to failed: {status_error}"
                     )
+                    with contextlib.suppress(Exception):
+                        await session.rollback()
                 documents_failed += 1
                 continue