diff --git a/backend/danswer/llm/utils.py b/backend/danswer/llm/utils.py
index 4be8e14640..58fd634d7c 100644
--- a/backend/danswer/llm/utils.py
+++ b/backend/danswer/llm/utils.py
@@ -42,7 +42,7 @@ def translate_danswer_msg_to_langchain(
     # If the message is a `ChatMessage`, it doesn't have the downloaded files
     # attached. Just ignore them for now. Also, OpenAI doesn't allow files to
     # be attached to AI messages, so we must remove them
-    if isinstance(msg, PreviousMessage) and msg.message_type != MessageType.ASSISTANT:
+    if not isinstance(msg, ChatMessage) and msg.message_type != MessageType.ASSISTANT:
         files = msg.files
     content = build_content_with_imgs(msg.message, files)