[Bug] macOS app update relaunch fails - manual reinstallation required

[JackCameo]

Bug Description
Claude UI for mac displays updates but when clicking the relaunch to install update it does not work. the app closes but does not install and or relaunch. I have to download it manually from the website and replace it to install updates.

Environment Info

• Platform: darwin
• Terminal: Apple_Terminal
• Version: 2.1.112
• Feedback ID: 907e2a14-f148-401a-b980-d5b562060b62

[github-actions]

Found 3 possible duplicate issues:

1. [BUG] Display issue + update loop: app stuck on "Relaunch to apply" after every restart #49699
2. Claude Desktop Squirrel auto-updater fails code signature validation on macOS 26 Tahoe (SQRLCodeSignatureErrorDomain) #41234
3. [Bug] Auto-updater fails to activate downloaded version and reverts manual symlink changes #41602

This issue will be automatically closed as a duplicate in 3 days.

• If your issue is a duplicate, please close it and 👍 the existing issue instead
• To prevent auto-closure, add a comment or 👎 this comment

🤖 Generated with Claude Code

[0xbrainkid]

macOS app update relaunch failing and requiring manual reinstallation is the companion issue to #50387 (ShipIt relaunching Claude after the user explicitly quit it). While #50387 documents the case where ShipIt launches when the user does not want it to, #50582 documents the case where ShipIt fails to launch when the user does want the update to apply.

Both failures have the same root cause: ShipIt's relaunch logic is brittle. It either relaunches when it should not (#50387) or fails to relaunch when it should (#50582).

The specific failure pattern for #50582: The update download succeeds and the updated binary is written to disk, but the app fails to relaunch with the new version. This leaves the user with a downloaded-but-not-active update — they must reinstall manually to get the updated version running.

What typically causes ShipIt relaunch failures on macOS:

1. Code signing failure: The new binary's code signature cannot be verified by Gatekeeper, preventing the relaunch.
2. Quarantine attribute: The downloaded binary has the quarantine extended attribute (com.apple.quarantine) and Gatekeeper blocks it.
3. App Bundle lock: The running app cannot be replaced because macOS file system holds a lock on the app bundle.

Diagnostic steps:

• Check Console.app for any Gatekeeper or code signing errors at the time of the update
• Run spctl --assess --verbose /Applications/Claude.app to check the signature
• Run xattr -l /Applications/Claude.app to check for quarantine attributes

This is the third update-related issue this week (#50387, #50564, #50582) — the update system needs a comprehensive reliability pass.

[gtirloni]

I was going to open a new issue but I think this one fits. Here's my bug report.

Hitting the same issue. Adding forensic detail from ShipIt_stderr.log in case it helps localize the failure.

Environment

• Claude Desktop (installed): 1.1617.0
• Claude Desktop (target): 1.3109.0
• macOS: 26.4
• Hardware: Apple Silicon
• Install location: /Applications/Claude.app (not translocated)

Reproduction

1. Run Claude Desktop 1.1617.0.
2. Accept the in-app update prompt. Download completes, "Relaunch" button appears.
3. Click Relaunch.
4. App reopens at 1.1617.0. Update prompt returns. Loop.

Clearing the in-app cache and re-authenticating had no effect. Quitting the app via Cmd+Q left /Applications/Claude.app/Contents/Helpers/chrome-native-host running, but killing it and relaunching did not break the loop.

Silent-success finding

Tail of ~/Library/Caches/com.anthropic.claudefordesktop.ShipIt/ShipIt_stderr.log:

2026-04-10 11:01:38 ShipIt Moved bundle contents from .../ShipIt.8LNB56fr/Claude.app
2026-04-10 11:01:38 ShipIt Moved bundle contents to /Applications/Claude.app/
2026-04-10 11:01:38 ShipIt Installation completed successfully
2026-04-10 11:01:40 ShipIt Successfully launched application at /Applications/Claude.app/

After this run, CFBundleShortVersionString remained 1.1617.0. ShipIt's bundle swap succeeded, but whatever was moved into place was the same version it replaced.

The log contains no entries after Apr 10 despite multiple update attempts over the following nine days. SQRLUpdater appears to be failing above the ShipIt layer without invoking it, leaving no log trace.

Observations

• Possibly thousands of builds between installed and target version, suggesting affected users have been stuck for weeks.
• No visible error surfaces to the user. The "Relaunch to update" prompt is the only signal and it behaves as if the update worked.
• Clearing caches, re-authenticating, and killing helper processes do not resolve it. Only a manual reinstall does.

Workaround

rm -rf ~/Library/Caches/com.anthropic.claudefordesktop
rm -rf ~/Library/Caches/com.anthropic.claudefordesktop.ShipIt
rm -rf /Applications/Claude.app
# download fresh DMG from claude.ai/download and reinstall

MCP config at ~/Library/Application Support/Claude/claude_desktop_config.json and Keychain credentials survive.

[github-actions]

Closing for now — inactive for too long. Please open a new issue if this is still relevant.

[github-actions]

This issue has been automatically locked since it was closed and has not had any activity for 7 days. If you're experiencing a similar issue, please file a new issue and reference this one if it's relevant.