Quick question: are you working over SSH? If so, could you try reproducing this locally (without SSH/Remote) to see if it still happens?
It also looks like you may be hitting a file size limit when attaching files to chat. Cursor has limits on attachment size, and for .ipynb files, 8 MB can exceed that limit.
Could you please:
Check if this reproduces in a local project (no SSH/Remote)?
Share the exact size of the .ipynb file.
Check Developer Tools console (Help > Toggle Developer Tools) while trying to attach it. Do you see any errors?