[BUG] **Title:** Claude Desktop loses active session when app relaunches for update — no warning, no recovery

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?

Platform: Claude Desktop (Mac)

Describe the problem:

When Claude Desktop prompts to relaunch for an update and the user accepts, the entire active session context is permanently lost with no way to recover it. There is no warning that session content will be deleted, no auto-save, and no backup. For users doing multi-step work (file operations, pipelines, long conversations with important outputs), this is a significant data loss event.

What I lost:

I lost an active working session mid-task after accepting the relaunch prompt. The work was not recoverable.

What I expected:

Either (1) the session should persist after relaunch, or (2) I should receive a clear warning before relaunch that says "your current session will be permanently lost" so I can save my work first.

Suggested fixes (any one of these would help):

Save session state to disk before relaunching, restore it after update
Show a clear warning: "Relaunching will permanently delete your current session. Save your work before continuing."
Add a "Save conversation" export button so users can back up before relaunch
Change "Relaunch Now" to default to "Later" so users aren't accidentally caught mid-task
Why this matters:

Claude Desktop is used for serious technical work (file pipelines, MCP tool sessions, long multi-step tasks). Losing a session mid-task is not a minor inconvenience — it can mean hours of work lost with no recourse. The web version saves conversations automatically; the desktop version should have equivalent protection.

What Should Happen?

Before any relaunch or update, the app should either (1) automatically save the current session to disk and restore it after the update completes, or (2) show a clear warning dialog that says "Relaunching will permanently delete your current session — save your work before continuing" with a visible "Save & Relaunch" or "Remind Me Later" option. The default button should be "Later," not "Relaunch Now," so users are not accidentally caught mid-task. The web version of Claude automatically preserves all conversations — the desktop app should have equivalent protection.

Error Messages/Logs

Working directory no longer exists: /Users/eliza/Documents/Claude/Projects/build a new website. The folder may have been moved, deleted, or unmounted.

Steps to Reproduce

Open Claude Desktop and start an active working session (multi-step task, file operations, or long conversation with important content)
While mid-session, a notification appears asking to relaunch the app for an update
Click "Relaunch" or accept the update prompt
App closes and relaunches with the update applied
The previous session is completely gone — no restore, no recovery, no warning was given before step 3 that this would happen
Expected: Session is restored after relaunch, OR a warning appeared in step 2 saying the session would be lost.

Actual: Session is permanently deleted with no warning and no way to recover.

Claude Model

Opus

Is this a regression?

I don't know

Last Working Version

_No response_

Claude Code Version

opus 4.8

Platform

Anthropic API

Operating System

macOS

Terminal/Shell

Terminal.app (macOS)

Additional Information

_No response_