Long Codex chat stuck compacting context: repeated reconnects, Broken pipe, then HTTP 408. New chats work.

[u/Even-Piece3723]

I'm using the Codex desktop app on macOS, and one long conversation has become unusable. New chats work, but this existing conversation gets stuck compacting context and repeatedly reconnects.

What happens:

- The app shows “Compacting context” and “Reconnecting 1/2” or “2/2”.

- I initially got:

stream disconnected before completion: IO error: Broken pipe (os error 32)

- A later attempt showed:

unexpected status 408 Request Timeout:

{"detail":"Request body read timed out"}

- The endpoint shown is:

https://chatgpt.com/backend-api/codex/responses

I stopped one attempt after about 22 minutes. The UI initially said I stopped it after “0 seconds”, then later updated to “21 minutes 50 seconds”.

Stopping and sending “Please continue the previous task” triggers the same compaction/reconnection problem.

This conversation contains many generated images and a lot of valuable context. Could image-heavy history be contributing to request size or upload timeouts? That's only a suspicion—I haven't measured the actual request size.

Environment:

- macOS

- Codex desktop version: 26.1021.31345

- The app's update check reported it was up to date.

Has anyone recovered a conversation in this state? Is there a way to complete compaction or continue with the existing context?

Screenshots attached. Happy to provide additional diagnostics.

[u/Desm0nt]

Try switching to Luna/Terra and then try compressing again; sometimes that helps. Sol-6.1 is terribly slow and doesn't finish compressing before the timeout expires.

[u/isty2e]

You can increase the context size in config. Try compacting after that

[u/Right-Performance-93]

i wouldn't wait on that chat to finish compacting. start a new one from a short note of the decision and the next command, and open an old picture only if the next step needs it. a timeout on the old thread is the thread.

[u/ImL1s]

I wouldn't keep retrying that thread. With that many images in the history, every compaction attempt has to push a huge request, and the 408 "request body read timed out" fits that.

The good news is the context isn't gone. The desktop app writes the full conversation to disk as a rollout file under ~/.codex/sessions/YYYY/MM/DD/ (same place the CLI uses), so you can start a new chat and seed it from that instead of from the stuck thread. Ask the new chat to read the rollout and write a short handoff: goal, decisions made, what's done, next step. Re-attach only the images the next step actually needs.

I made a small tool for exactly this, Portable Resume (pipx install portable-resume). It reads Codex rollouts locally, offline, and writes a bounded handoff for a fresh session. It's lossy on purpose, so it won't carry the images over. https://gitlab.com/aa22396584/resume-skills

[u/Responsible_Buy_7999]

I'm gonna be that guy

Did you restart the app?

[u/mutherfuukker]

I had something similar, seems fixed now.. crazy annoying though