[macOS][ChatGPT Desktop] ZIP attachments fail with generic “Upload failed” in ordinary Chat
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Description
What version of the Codex App are you using?
ChatGPT/Codex Desktop 26.814.41407.
What subscription do you have?
ChatGPT Pro.
What platform is your computer?
macOS on Apple Silicon.
What issue are you seeing?
In ordinary Chat in the ChatGPT desktop app, ZIP attachments are accepted by the file picker and appear as attachment cards, but then fail with the generic message “Upload failed.”
I reproduced this with two separate .zip files in the same desktop session.
This appears to corroborate the currently open issue #39203, which reports the same desktop ZIP-upload failure and records an application/zip finalization rejection with HTTP 415 unsupported_mime_type.
OpenAI’s current file-upload documentation lists common supported document, spreadsheet, presentation, and text formats, but does not clearly state whether .zip is supported in ordinary Chat.
What steps can reproduce the bug?
- Open an ordinary Chat in ChatGPT Desktop on macOS.
- Select a
.zipfile using the attachment picker. - The app accepts the file and creates an attachment card.
- Wait for upload processing.
- The card changes to “Upload failed.”
- Repeat with another
.zipfile; the same failure occurs.
What is the expected behavior?
If ZIP attachments are supported, the archive should upload successfully.
If ZIP attachments are intentionally unsupported, the desktop file picker should reject the file before upload begins and clearly explain that the format is unsupported instead of accepting it and later showing a generic upload failure.
Additional information
In-app feedback was submitted for this reproduction:
no-active-thread-01a01c6d-e27f-74d3-8e42-c93e5969d0c4
Related open issue: #39203.
Contributor guide
First steps
- Read the whole issue, then the project's contributing guide.
- Comment on the issue to say you are picking it up — it saves two people doing the same work.
- Fork the repository and make your change on a branch.
- Open a pull request that references the issue number.
Research direction
No source files or tests are named. First reproduce the ZIP upload failure in ordinary Chat on macOS, then compare the desktop attachment-picker and upload handling with issue #39203. Done means ZIP files either upload successfully or are rejected before upload with a clear unsupported-format message.
Written by the indexing model from the issue text.
Assessment
- Tech stack
- macos
- Domain
- desktop
- Issue type
- Bug
- Difficulty
- 4/5
- Estimated time
- 3-5 days
- Activity status
- Active
- Clarity
- Mostly clear
- Newbie friendliness
- 42/100