PDF Won’t Upload and Crashes Each Time
OpenAI Developer Community
April 18, 2026
I am a ChatGPT Plus user experiencing persistent file upload failures for over 48 hours.
Issue details:
* PDF uploads return error: “File upload failed. The server is having problems (500 error)”
* Image uploads (JPG/PNG) do not complete and remain stuck with spinning icons
* This occurs across:
* New threads
* After app reinstall
* After logging out and back in
Environment:
* iPhone (iOS latest version)
* ChatGPT mobile app (latest version)
* Both WiFi and cellular tested
Additional notes:
* Previously, saving/re-encoding PDFs allowed upload, but now all uploads fail
* Issue is consistent and reproducible
Request:
Please who do I contact to investigate potential account-level or session-level upload restrictions or backend failures affecting my account.
Discussion in the ATmosphere