[macOS] Appshot opens a new chat and fails with “Unable to attach appshot”

What subscription do you have?

ChatGPT Plus.

What platform is your computer?

macOS on an Intel MacBook Pro, using the ChatGPT/Codex desktop app in Work mode.

What issue are you seeing?

Appshots cannot be attached reliably. Pressing the left and right Command keys together opens a new chat instead of attaching the appshot to the current chat, even when the current chat was used less than 60 seconds earlier.

The new chat then shows the red error message:

Impossibile allegare l'appshot

("Unable to attach the appshot.")

As a result, ChatGPT/Codex has been unable to acquire or receive the user's screen context for approximately two weeks. Computer Use has also repeatedly appeared disabled/unavailable during this period.

Steps to reproduce

1. Open an existing conversation in the ChatGPT/Codex desktop app.
2. Select Work mode.
3. Send a message in that conversation.
4. Within 60 seconds, bring another application window to the foreground.
5. Press the left and right Command keys simultaneously.
6. Observe that a new chat opens rather than attaching the appshot to the active/recent conversation.
7. Observe the red error: "Impossibile allegare l'appshot".

The issue persists after restarting the app and retrying the documented procedure.

Expected behavior

The appshot should be attached to the conversation used within the previous 60 seconds, as described in the official Appshots documentation. The screenshot and available window text should then be accessible in that same conversation.

Actual behavior

A new chat opens and the appshot attachment fails with "Impossibile allegare l'appshot", leaving ChatGPT unable to access the screen context.

Impact

This blocks normal Appshots and screen-context workflows entirely and has persisted for about two weeks.

No source file, test, or entry point is identified. Start by reproducing the shortcut flow in the macOS desktop app and compare it with the documented Appshots behavior; done means an appshot attaches to the recently used conversation instead of opening a new chat or showing the error.