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PDF Won’t Upload and Crashes Each Time

OpenAI Developer Community April 18, 2026
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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.

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