#GPT chat file uploads fail in macOS and iPadOS apps

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glossy thistleBOT
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Reported by @ocean umbra

Bug Report: GPT chat file uploads fail in macOS and iPadOS apps
`Steps to Reproduce`
  1. Open the ChatGPT app on macOS or iPadOS
  2. Open any GPT chat
  3. Try to upload a file (JPG, TXT, PDF, DOC)
  4. The upload fails with a 500 error

This happens across multiple GPTs.
Normal chats work.
GPT uploads on the web work.

`Expected Result`

Files should upload successfully inside GPT chats in the macOS and iPadOS apps.

`Actual Result`

Uploads fail only inside GPT chats in the macOS and iPadOS apps with:
"The server is having issues. Please try again later. (500, ...)"
Normal chats can upload files, and GPT uploads work on the web.

`Environment`
  • macOS app: macOS 14.4.1 (23E224) - iPad: iPad mini (5th generation), iPadOS 26.3.1(a) - Browser/web: GPT uploads work - File types tested: JPG, TXT, PDF, DOC
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Additional Information

Please provide relevant details to help resolve the issue, such as:

  • ChatGPT Shared Link (if applicable).
  • Screenshots or videos demonstrating the problem.

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