diff --git a/src/documents/bulk_edit.py b/src/documents/bulk_edit.py
index 1aba8f9ec..2e3e5f591 100644
--- a/src/documents/bulk_edit.py
+++ b/src/documents/bulk_edit.py
@@ -159,13 +159,20 @@ def modify_custom_fields(doc_ids: list[int], add_custom_fields, remove_custom_fi
 
 @shared_task
 def delete(doc_ids: list[int]):
-    Document.objects.filter(id__in=doc_ids).delete()
+    try:
+        Document.objects.filter(id__in=doc_ids).delete()
 
-    from documents import index
+        from documents import index
 
-    with index.open_index_writer() as writer:
-        for id in doc_ids:
-            index.remove_document_by_id(writer, id)
+        with index.open_index_writer() as writer:
+            for id in doc_ids:
+                index.remove_document_by_id(writer, id)
+    except Exception as e:
+        if "Data too long for column" in str(e):
+            logger.warning(
+                "Detected a possible incompatible database column. See https://docs.paperless-ngx.com/troubleshooting/#convert-uuid-field",
+            )
+        logger.error(f"Error deleting documents: {e!s}")
 
     return "OK"
 
diff --git a/src/documents/tests/test_bulk_edit.py b/src/documents/tests/test_bulk_edit.py
index d80116a80..c6e846a77 100644
--- a/src/documents/tests/test_bulk_edit.py
+++ b/src/documents/tests/test_bulk_edit.py
@@ -327,6 +327,15 @@ class TestBulkEdit(DirectoriesMixin, TestCase):
         )
         self.assertEqual(groups_with_perms.count(), 2)
 
+    @mock.patch("documents.models.Document.delete")
+    def test_delete_documents_old_uuid_field(self, m):
+        m.side_effect = Exception("Data too long for column 'transaction_id' at row 1")
+        doc_ids = [self.doc1.id, self.doc2.id, self.doc3.id]
+        bulk_edit.delete(doc_ids)
+        with self.assertLogs(level="WARNING") as cm:
+            bulk_edit.delete(doc_ids)
+            self.assertIn("possible incompatible database column", cm.output[0])
+
 
 class TestPDFActions(DirectoriesMixin, TestCase):
     def setUp(self):