diff --git a/surfsense_backend/app/tasks/connector_indexers/google_drive_indexer.py b/surfsense_backend/app/tasks/connector_indexers/google_drive_indexer.py
index d67665d99..74101ed74 100644
--- a/surfsense_backend/app/tasks/connector_indexers/google_drive_indexer.py
+++ b/surfsense_backend/app/tasks/connector_indexers/google_drive_indexer.py
@@ -150,7 +150,7 @@ async def _should_skip_file(
         return True, f"File renamed: '{old_name}' → '{file_name}'"
 
     if not DocumentStatus.is_state(existing.status, DocumentStatus.READY):
-        return False, None
+        return True, "skipped (previously failed)"
     return True, "unchanged"
 
 
diff --git a/surfsense_backend/tests/integration/indexing_pipeline/test_drive_pipeline.py b/surfsense_backend/tests/integration/indexing_pipeline/test_drive_pipeline.py
index 77128ebd9..2fffa9053 100644
--- a/surfsense_backend/tests/integration/indexing_pipeline/test_drive_pipeline.py
+++ b/surfsense_backend/tests/integration/indexing_pipeline/test_drive_pipeline.py
@@ -110,10 +110,10 @@ async def test_drive_legacy_doc_migrated(
     assert row.unique_identifier_hash == native_hash
 
 
-async def test_should_skip_file_does_not_skip_failed_document(
+async def test_should_skip_file_skips_failed_document(
     db_session, db_search_space, db_user,
 ):
-    """A FAILED document with unchanged md5 must NOT be skipped — it needs reprocessing."""
+    """A FAILED document with unchanged md5 must be skipped — user can manually retry via Quick Index."""
     import importlib
     import sys
     import types
@@ -164,6 +164,7 @@ async def test_should_skip_file_does_not_skip_failed_document(
 
     incoming_file = {"id": file_id, "name": "Failed File.pdf", "mimeType": "application/pdf", "md5Checksum": md5}
 
-    should_skip, _msg = await _should_skip_file(db_session, incoming_file, space_id)
+    should_skip, msg = await _should_skip_file(db_session, incoming_file, space_id)
 
-    assert not should_skip, "FAILED documents must not be skipped even when content is unchanged"
+    assert should_skip, "FAILED documents must be skipped during automatic sync"
+    assert "failed" in msg.lower()