claude-code - 💡(How to fix) Fix [BUG] Claude Desktop 1.6608.0 (macOS): All rewind attempts rejected with "Can't rewind to this message" — regression after auto-update

Preflight Checklist

• I have searched existing issues and this hasn't been reported yet
• This is a single bug report
• I am using the latest version of Claude Code

What's Wrong?

In Claude Desktop 1.6608.0 on macOS, every rewind attempt is rejected with the popup "Can't rewind to this message" — including in a freshly created empty conversation with only 2 user messages exchanged. The rewind picker renders normally and shows anchor candidates, but selecting any anchor triggers the rejection popup.

This affects every conversation — fresh, resumed, native, or imported — and every message position, not just the first message. So this is a much broader failure than:

• #50780 (Desktop first-message-only)
• #48955 (CLI-origin messages via /desktop only)

The same machine's terminal Claude Code (CLI) rewind continues to work correctly, isolating the regression to the Desktop client.

What Should Happen?

Selecting an anchor in the rewind picker should restore the conversation (and optionally code) to the point before that message, as it did before the 1.6608.0 update.

Error Messages/Logs

~/Library/Logs/Claude/main.log shows two repeating patterns on every rewind attempt today:

2026-05-08 15:34:14 [info] LocalSessions.rewind: sessionId=local_0614a145-... target=e88e4bcb-...
      at dE.rewindSession (/Applications/Claude.app/Contents/Resources/app.asar/.vite/build/index.js:2420:4427)
      at Object.rewind (/Applications/Claude.app/Contents/Resources/app.asar/.vite/build/index.js:2506:4220)
2026-05-08 15:34:14 [info] [Rewind] No rewind point for local_0614a145-... target=e88e4bcb-... (assistantUuid=none, hasText=true)

2026-05-08 15:40:35 [info] [Rewind] target=9c70ad22-... → assistantUuid=ac2cc93a-... not on active chain for local_c0799054-... (chain size 2/14)

Earlier in the day on a long-running conversation: chain size 4/178 — only 4 of 178 messages on active chain. New empty conversations show the assistantUuid=none, hasText=true variant.

All rewind calls today route through LocalSessions.rewind (client-side path).

Steps to Reproduce

1. Open Claude Desktop 1.6608.0 on macOS
2. Start a fresh conversation (Cmd+N)
3. Send a short message ("hi") and wait for response
4. Send another short message and wait for response (now there are 2 user + 2 assistant messages)
5. Press Esc Esc (or click rewind button) — picker renders with anchors
6. Select any anchor
7. Popup: "Can't rewind to this message"

Reproduces 100% on every conversation tested.

Claude Model

Sonnet (default)

Is this a regression?

Yes, this worked in a previous version

Last Working Version

Pre-1.6608.0 — regression appeared after Claude Desktop auto-update on 2026-05-07.

Claude Code Version

Claude Desktop 1.6608.0 (CFBundleShortVersionString from /Applications/Claude.app/Contents/Info.plist, mtime 2026-05-07 14:33)

Platform

Anthropic API

Operating System

macOS

Additional Context

• All [Rewind] log entries today route through LocalSessions.rewind (client-side path), suggesting a client-side validation regression rather than a server-side rejection.
• assistantUuid=none, hasText=true indicates the user message lacks a paired assistant UUID in client memory — Desktop now treats this as a hard reject. Previous behavior was apparently more lenient.
• The not on active chain (chain size N/M) pattern suggests parentUuid chain validation has been tightened, rejecting messages whose ancestor chain the client cannot fully resolve.
• Confirmed plugin SessionStart hooks (superpowers v5.1.0) are not the cause: bug persists after disabling plugin hooks and restarting Desktop.
• Same machine, same day, same account: terminal Claude Code (CLI) rewind works correctly.

Related issues (similar but distinct)

• #50780 — Desktop cannot rewind first message (this bug rejects every message)
• #48955 — Desktop rewind breaks for CLI-origin messages (this bug rejects native Desktop messages too)
• #44828 — isMeta:true filter (this bug surfaces a different rejection path: assistantUuid=none and not on active chain)