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Codex Issues / #39233

[ChatGPT Desktop] Project chat cannot be re-pinned after unpinning; same chat pins normally on Web

Open 💬 1 comment Opened Aug 18, 2026 by omarpinarecords

What issue are you seeing?

In the ChatGPT Desktop app, an existing ordinary Chat inside a ChatGPT Project cannot be pinned again after it has been unpinned.

The Desktop app shows this toast:

You cannot pin a project or GPT conversation.

This is incorrect for the affected object: it is an ordinary project chat, not a Project object and not a custom GPT conversation.

The same exact chat can be pinned normally on chatgpt.com with no error. That isolates the failure to the Desktop surface rather than the chat's server-side pin eligibility.

Environment

  • Surface with failure: ChatGPT Desktop app on macOS
  • Mode: Chat
  • Context: ChatGPT Project
  • Plan: ChatGPT Pro 20x
  • Observed: August 18, 2026
  • Desktop build: 26.814.41407

Steps to reproduce

  1. Have an ordinary Chat inside a ChatGPT Project that is already pinned.
  2. Unpin that chat in ChatGPT Desktop.
  3. In Desktop, open the chat's menu and choose Pin chat again.
  4. Observe the toast:

You cannot pin a project or GPT conversation.

  1. Open the same exact chat on chatgpt.com.
  2. Choose Pin chat.
  3. The chat pins successfully on Web with no error.

Expected behavior

An eligible ordinary Chat inside a ChatGPT Project should be pinnable from Desktop, matching Web behavior and current OpenAI documentation.

Current Projects documentation states that users can pin a chat even when newer chats appear in the project:

https://learn.chatgpt.com/docs/projects

ChatGPT Release Notes also document pinning chats and projects from the sidebar:

https://help.openai.com/en/articles/6825453-chatgpt-release-notes

Actual behavior

  • Web: same chat pins successfully.
  • Desktop: same chat is rejected with You cannot pin a project or GPT conversation.
  • The chat remains in the Project and otherwise works normally.

This looks like a Desktop-side object-type / pin-eligibility classification regression or stale client state. The exact internal cause is not proven.

In-product feedback and performance trace

The same reproduction was submitted through /feedback on August 18, 2026.

Feedback ID:

no-active-thread-01a015fb-db31-7171-b442-2aef5fb5607b

A performance trace was also uploaded for this reproduction.

Performance trace ID:

no-active-thread-01a01600-efa4-7d53-9e75-c5c0f92a704c

Related issue

  • #38943 concerns ChatGPT Web pin state affecting Recents/sidebar rendering. It is related to pin/sidebar behavior but is not the same reproduction; this issue is specifically a Desktop-only failure to re-pin an otherwise eligible Project chat while Web succeeds.

Requested investigation

Please compare the Desktop and Web pin-eligibility/object-type checks for chats that belong to ChatGPT Projects, especially after an unpin → re-pin transition. Desktop should not classify an ordinary project chat as an ineligible Project/GPT conversation when the same server-side chat is accepted by Web.

View original on GitHub ↗

1 Comment

omarpinarecords · 2 days ago

Follow-up testing update (macOS Desktop, August 25, 2026):

  • Several control conversations across Project and projectless contexts could be pinned and unpinned successfully.
  • One additional Pin action did not capture a same-conversation state transition or the reported error, so it is not being counted as a reproduction.
  • The recording therefore adds useful negative controls, but it does not yet provide a decisive matched unpin → re-pin outcome for the exact originally affected ordinary Project chat.
  • The original reported comparison remains unchanged: the affected ordinary Project chat was rejected by Desktop with You cannot pin a project or GPT conversation., while the same chat was accepted on Web.

The linked OpenAI Support case was also updated. Support was asked to independently test the relevant Desktop scenarios, document the exact build/configuration and evidence if they cannot reproduce, provide their reproduction procedure, and offer a screen-sharing session if asynchronous troubleshooting is insufficient.

No private chat titles, recordings, screenshots, or Support correspondence are attached here.