diff --git a/backend/danswer/background/celery/tasks/vespa/tasks.py b/backend/danswer/background/celery/tasks/vespa/tasks.py
index c43de3a85..e958d63ad 100644
--- a/backend/danswer/background/celery/tasks/vespa/tasks.py
+++ b/backend/danswer/background/celery/tasks/vespa/tasks.py
@@ -31,6 +31,7 @@ from danswer.db.connector_credential_pair import get_connector_credential_pair_f
 from danswer.db.connector_credential_pair import get_connector_credential_pairs
 from danswer.db.document import count_documents_by_needs_sync
 from danswer.db.document import get_document
+from danswer.db.document import get_document_ids_for_connector_credential_pair
 from danswer.db.document import mark_document_as_synced
 from danswer.db.document_set import delete_document_set
 from danswer.db.document_set import delete_document_set_cc_pair_relationship__no_commit
@@ -363,7 +364,7 @@ def monitor_connector_deletion_taskset(
 
     count = cast(int, r.scard(rcd.taskset_key))
     task_logger.info(
-        f"Connector deletion progress: cc_pair_id={cc_pair_id} remaining={count} initial={initial_count}"
+        f"Connector deletion progress: cc_pair={cc_pair_id} remaining={count} initial={initial_count}"
     )
     if count > 0:
         return
@@ -372,16 +373,27 @@ def monitor_connector_deletion_taskset(
         cc_pair = get_connector_credential_pair_from_id(cc_pair_id, db_session)
         if not cc_pair:
             task_logger.warning(
-                f"monitor_connector_deletion_taskset - cc_pair_id not found: cc_pair_id={cc_pair_id}"
+                f"Connector deletion - cc_pair not found: cc_pair={cc_pair_id}"
             )
             return
 
         try:
+            doc_ids = get_document_ids_for_connector_credential_pair(
+                db_session, cc_pair.connector_id, cc_pair.credential_id
+            )
+            if len(doc_ids) > 0:
+                # if this happens, documents somehow got added while deletion was in progress. Likely a bug
+                # gating off pruning and indexing work before deletion starts
+                task_logger.warning(
+                    f"Connector deletion - documents still found after taskset completion: "
+                    f"cc_pair={cc_pair_id} num={len(doc_ids)}"
+                )
+
             # clean up the rest of the related Postgres entities
             # index attempts
             delete_index_attempts(
                 db_session=db_session,
-                cc_pair_id=cc_pair.id,
+                cc_pair_id=cc_pair_id,
             )
 
             # document sets
@@ -398,7 +410,7 @@ def monitor_connector_deletion_taskset(
                 noop_fallback,
             )
             cleanup_user_groups(
-                cc_pair_id=cc_pair.id,
+                cc_pair_id=cc_pair_id,
                 db_session=db_session,
             )
 
@@ -420,20 +432,21 @@ def monitor_connector_deletion_taskset(
                 db_session.delete(connector)
             db_session.commit()
         except Exception as e:
+            db_session.rollback()
             stack_trace = traceback.format_exc()
             error_message = f"Error: {str(e)}\n\nStack Trace:\n{stack_trace}"
-            add_deletion_failure_message(db_session, cc_pair.id, error_message)
+            add_deletion_failure_message(db_session, cc_pair_id, error_message)
             task_logger.exception(
                 f"Failed to run connector_deletion. "
-                f"cc_pair_id={cc_pair_id} connector_id={cc_pair.connector_id} credential_id={cc_pair.credential_id}"
+                f"cc_pair={cc_pair_id} connector={cc_pair.connector_id} credential={cc_pair.credential_id}"
             )
             raise e
 
     task_logger.info(
         f"Successfully deleted cc_pair: "
-        f"cc_pair_id={cc_pair_id} "
-        f"connector_id={cc_pair.connector_id} "
-        f"credential_id={cc_pair.credential_id} "
+        f"cc_pair={cc_pair_id} "
+        f"connector={cc_pair.connector_id} "
+        f"credential={cc_pair.credential_id} "
         f"docs_deleted={initial_count}"
     )
 
diff --git a/backend/danswer/db/document_set.py b/backend/danswer/db/document_set.py
index 0ba6c4e9a..b5af99b22 100644
--- a/backend/danswer/db/document_set.py
+++ b/backend/danswer/db/document_set.py
@@ -398,7 +398,7 @@ def mark_document_set_as_to_be_deleted(
 
 def delete_document_set_cc_pair_relationship__no_commit(
     connector_id: int, credential_id: int, db_session: Session
-) -> None:
+) -> int:
     """Deletes all rows from DocumentSet__ConnectorCredentialPair where the
     connector_credential_pair_id matches the given cc_pair_id."""
     delete_stmt = delete(DocumentSet__ConnectorCredentialPair).where(
@@ -409,7 +409,8 @@ def delete_document_set_cc_pair_relationship__no_commit(
             == ConnectorCredentialPair.id,
         )
     )
-    db_session.execute(delete_stmt)
+    result = db_session.execute(delete_stmt)
+    return result.rowcount  # type: ignore
 
 
 def fetch_document_sets(