Chat / Work Cloud fails on the first prompt in one project since DevDay; other projects work

ChatGPT Bugs
1

Work Cloud currently fails to start a new session in one existing ChatGPT project. The same minimal prompt works without a project and in other existing projects. Work Local works in every project I tested.

I first noticed the problem when the DevDay presentation began and new features were being rolled out. There was wider service instability that day, so I initially assumed it was temporary load. The failure continued after the status page returned to green. The timing is an observation; the cause is still unknown.

Latest isolation tests: October 4–5, 2026 (UTC+4). Project names below are anonymized.

Context Result with a new Work Cloud session
No project Starts and responds
Other existing projects tested Starts and responds
Project A (affected) Fails on the first prompt, before any visible assistant response

Steps to reproduce

  1. Open the affected existing project.
  2. Select Work Cloud and start a new conversation.
  3. Send work cloud working test.

Expected: the session starts and responds.

Actual: Hmm...something seems to have gone wrong.

The same project-dependent behavior occurs in the web version and the macOS Desktop app. The web failure was reproduced with both GPT-6.1 Sol / Max and GPT-6 Luna / Light.

Sources comparison and Google Drive test

Project Total Sources Uploaded files Saved responses Drive sources
A (affected) 27 11 15 1
B (working control) 15 7 8 0

Both projects use Default memory. The total Sources count includes saved responses and is different from the uploaded-file count.

I temporarily removed only the Google Drive source from Project A, reloaded, and verified 26 Sources / 0 Drive sources. A fresh Work Cloud session still failed. I then restored the exact same file/link, completed a fresh sync, and verified 27 Sources / 1 Drive source. A fresh Cloud session still failed. The underlying Drive file was left intact.

Removing the Drive source did not resolve the observed failure. A project-specific initialization, context, or source-processing problem remains a possibility, but no root cause has been established.

Earlier Support request to test a new Cloud Work task.

@OpenAI_Support Could the Work Cloud team investigate why a fresh session fails only in this project and advise which diagnostic identifiers I should provide privately? Has anyone else reproduced this exact pattern?

The screenshot shows the minimal test after removing the Drive source. Private project/source names, links, account details, and chat history are excluded.

work-cloud-without-drive
work-cloud-without-drive790×165 7.87 KB

2

Hi @cryptocean, thanks for flagging this and sharing the detailed tests. It’s frustrating to have Work Cloud fail on the first prompt in one project when it works elsewhere.

This could be related to the elevated Work Mode errors reported on October 5, which have since been resolved, as noted on the Status Page.

If it’s still happening, please email support@openai.com with:

  • The affected project ID/name and session ID.
  • The latest failure’s timestamp in UTC.
  • Any sanitized logs you have, if available.

These details will help Support investigate further. Please keep the logs and private project details out of this public thread.

- Yash

3

@OpenAI_Support I just retested today, October 9: Work Cloud still fails in the affected project on web, mobile and Desktop. I’ve emailed the project/session IDs, UTC timestamp, sanitized logs and a screenshot. No case-number acknowledgment has arrived yet. Roughly three recent Support email threads have received no reply, not even an automated case number. Could you confirm receipt and tell me how to get this traced?

4

Hi @cryptocean, thanks for the update. I understand it’s frustrating that Work Cloud still fails and you haven’t received an acknowledgment of your emails.

I can’t confirm receipt from this thread. Please double-check that the email was sent from your intended address to support@openai.com.

You can also sign in at help.openai.com and use the chat bubble in the bottom-right corner to contact Support.

- Yash

5

@OpenAI_Support I checked Sent and the recipient address. Before today’s follow-up, eight emails across four new Support threads since DevDay had received no reply or automated case acknowledgment, including in Spam/Trash. I’ve now followed up in the original thread and contacted Help Center.

October 14 clarification: ordinary Chat and Work Cloud both fail in this one Project on every platform: web, mobile and Desktop. This affects all existing conversations and newly created ones. Only Work Local works. Even a simple “test” returns “Hmm…something seems to have gone wrong.” I sent the private IDs, test link and cropped screenshot by email.

Could you check whether my emails reach your ticketing system and get this Project investigated? It’s blocking normal use.

Minimal Chat test and error
Minimal Chat test and error1570×339 13.2 KB

6

@OpenAI_Support October 14 update: this is resolved for me. Removing one unreadable entry from Project Sources restored old and new Chat / Work Cloud sessions. I kept the Library file and also confirmed recovery in the mobile app.

This is still a bug: why did the Source become unreadable, and why did it block the entire Project? Please investigate that.

Thanks @aswdxct.sky for the workaround that finally made this project usable again.

7

Hi @cryptocean, thanks for the update. Glad your Chat and Work Cloud sessions are working again, and thanks @aswdxct.sky for sharing the workaround!

This sounds similar to an issue we’re tracking where project chats fail because of missing connections to Library files. We haven’t confirmed why the source became unreadable or blocked your project, but we’ll share your findings with the team for review.

- Yash