[macOS app] Pasted images repeatedly fail to upload while the web app works normally #55649

Summary

In the ChatGPT/Codex macOS app, an image pasted from the clipboard into the message composer fails to upload. The attachment card shows Upload failed with a Retry action, but retrying multiple times does not resolve the failure.

The same image uploads normally in the ChatGPT web app, so the problem appears specific to the macOS app.

Environment

• App: ChatGPT for macOS (Powered by Codex & OWL)
• Version: 26.1013.40934
• App release date: October 16, 2026
• Subscription: ChatGPT Pro
• macOS: Golden Gate 27.0.1
• Hardware: 16-inch MacBook Pro, Apple M5 Max, 128 GB memory
• Observed on: October 20, 2026

Steps to reproduce

1. Open a conversation in the macOS app.
2. Copy an image to the clipboard.
3. Paste the image into the message composer.
4. Attempt to upload or send it.
5. Observe that the attachment shows Upload failed.
6. Click Retry multiple times.

Actual behavior

The pasted image remains in a failed state and cannot be uploaded, even after repeated retry attempts.

Expected behavior

The pasted image should upload successfully, matching the behavior of the ChatGPT web app.

Frequency

Reproduced repeatedly across multiple attempts in the macOS app. The same image uploads successfully on the web.

Impact

This blocks the normal clipboard-to-chat image workflow and forces users to switch to the browser whenever they need to attach a pasted image.

Regression

I cannot confirm the first affected version.

Error shown

Upload failed