Steps to Reproduce:
- Start a new chat and attach a file.
- Ask the assistant to use that file (e.g. “quiz me from the attached file, start from question 18, keep score
”).
- Continue the conversation for a few turns.
Test file
Expected Result
The assistant still has access to the previously attached document and can reference it without requiring the user to re-upload or paste its contents.
Actual Result
After a very few turns the system context no longer lists the uploaded document.
The model can lose the content of the file in just two exchanges, o3 seems to be the only model that stops and explicitly asks for the file to be attached again because it doesn't have access to it.
This evidently doesn't happen with the official apps from the model providers
Examples
https://kagi.com/assistant/70f3f629-88f1-40c0-b002-a6d4107c1eb4
https://kagi.com/assistant/d34359f5-6621-4216-9c91-254e0785c14d
https://kagi.com/assistant/fdda716c-e9a9-45b7-a720-926bd4d84aac
