[BUG] Pin option missing from session context menu for newly-created sessions (Claude for Windows desktop)

Preflight Checklist

• [x] I have searched existing issues and this hasn't been reported yet
• [x] This is a single bug report (please file separate reports for different bugs)
• [x] I am using the latest version of Claude Code

What's Wrong?

On the Claude for Windows desktop app, the per-session context menu (the dropdown from the session header) has no Pin/Unpin option at all for newly-created sessions. The menu shows only: Open in, Rename, Color, Transcript view, Fork, Archive, Delete (screenshot below).

Sessions created before the regression still retain their pinned/unpinned state — existing pins are not wiped — but there is no longer any way to pin or unpin a new session, because the menu entry is simply gone.

Additionally: running /clear on an old session that was already pinned makes it lose the Pin/Unpin menu option too — but it stays pinned. The result is a session stuck in the "Pinned" section with no way to unpin it from the context menu.

<img width="1277" height="440" alt="Image" src="https://github.com/user-attachments/assets/f6a88a34-6c3c-4dc0-b0b9-d48a4f00aeae" />

Note: this appears unrelated to the routines-sidebar regression (#54524) and the "pins wiped to empty array" reports (#54806). Those concern scheduled-routine sessions or existing pins being lost. This is the Pin control itself being absent from regular (non-routine) sessions.

What Should Happen?

Newly-created sessions should have a Pin/Unpin option in the session context menu, identical to sessions created before the regression.

Error Messages/Logs

Steps to Reproduce

Scenario A — new session:

1. In the Claude for Windows desktop app, create a new session.
2. Open the session header dropdown (chevron next to the session name).
3. Observe: no Pin/Unpin item in the menu.
4. Open the same dropdown on a session created before the regression — Pin/Unpin is present and works.

Scenario B — old, already-pinned session + /clear:

1. Take an old session that was pinned before the regression (it appears under "Pinned").
2. Run /clear in that session.
3. Open its context menu — the Pin/Unpin option is now gone, yet the session stays in the "Pinned" section with no way to unpin it.

<img width="1277" height="440" alt="Image" src="https://github.com/user-attachments/assets/c4be34ea-5fc8-4b9b-b05a-7fe52db08495" />

Troubleshooting already done: fully quit and relaunched the app; symptom persists.

Claude Model

Not sure / Multiple models

Is this a regression?

Yes, this worked in a previous version

Last Working Version

Unknown — broken across multiple recent builds; can't pinpoint the introducing version

Claude Code Version

Claude for Windows desktop 1.8555.2 (a476c3) — desktop app build (this is a desktop-UI bug, not the CLI)

Platform

Anthropic API

Operating System

Windows

Terminal/Shell

Other

Additional Information

Onset version unclear: this has been broken across multiple recent builds, so I can't pinpoint which version introduced it. Currently on Claude for Windows 1.8555.2 (a476c3), which is ahead of the published desktop changelog — no newer build available to update to.

Screenshot — the session context menu on a new session (only Open in, Rename, Color, Transcript view, Fork, Archive, Delete; no Pin entry):