diff --git a/llama_stack/providers/remote/files/s3/files.py b/llama_stack/providers/remote/files/s3/files.py
index 82ee1da83..5f436fe04 100644
--- a/llama_stack/providers/remote/files/s3/files.py
+++ b/llama_stack/providers/remote/files/s3/files.py
@@ -256,7 +256,8 @@ class S3FilesImpl(Files):
             content = response["Body"].read()
         except ClientError as e:
             if e.response["Error"]["Code"] == "NoSuchKey":
-                raise ResourceNotFoundError(row["id"], "File content", "files.list()") from e
+                await self.sql_store.delete("openai_files", where={"id": file_id})
+                raise ResourceNotFoundError(file_id, "File", "files.list()") from e
             raise RuntimeError(f"Failed to download file from S3: {e}") from e
 
         return Response(
diff --git a/tests/unit/providers/files/test_s3_files.py b/tests/unit/providers/files/test_s3_files.py
index 20eab1f51..640411b53 100644
--- a/tests/unit/providers/files/test_s3_files.py
+++ b/tests/unit/providers/files/test_s3_files.py
@@ -223,18 +223,13 @@ class TestS3FilesImpl:
         # Directly delete the S3 object from the backend
         s3_client.delete_object(Bucket=s3_config.bucket_name, Key=uploaded.id)
 
-        retrieved_metadata_after = await s3_provider.openai_retrieve_file(uploaded.id)  # TODO: this should fail
-        assert retrieved_metadata_after.id == uploaded.id
-
-        listed_files = await s3_provider.openai_list_files()
-        assert uploaded.id in [file.id for file in listed_files.data]
-
         with pytest.raises(ResourceNotFoundError, match="not found") as exc_info:
             await s3_provider.openai_retrieve_file_content(uploaded.id)
-
-        assert "content" in str(exc_info).lower()
         assert uploaded.id in str(exc_info).lower()
 
+        listed_files = await s3_provider.openai_list_files()
+        assert uploaded.id not in [file.id for file in listed_files.data]
+
     async def test_upload_file_s3_put_object_failure(self, s3_provider, sample_text_file, s3_config, s3_client):
         """Test that put_object failure results in exception and no orphaned metadata."""
         sample_text_file.filename = "test_s3_put_object_failure"