Desktop: session in a worktree of a trusted repo is permanently stuck on "workspace isn't trusted" — trust dialog never shown (app/CLI trust deadlock) #96928

Summary

A desktop-app session whose cwd is a git worktree under an already-trusted repo can get permanently stuck on "This workspace isn't trusted" — the trust dialog never appears, and "Try again" can never succeed. The app and the CLI disagree about what "trusted" means, and each waits for the other.

Environment

• Claude Code desktop app (macOS, Darwin 25.6.0)
• CLI v2.1.144 on the same machine
• Session created by the app in .claude/worktrees/<name> under a repo whose root is trusted (hasTrustDialogAccepted: true in ~/.claude.json)

What happens

1. Desktop session's cwd is <repo>/.claude/worktrees/<name>. That exact path has no entry under projects in ~/.claude.json (sibling worktrees have entries; this one was missed — cause unknown, session dates from June).
2. Opening the session shows the toast: "This workspace isn't trusted. If you trust this workspace, try again and choose Trust workspace when asked."
3. Clicking Try again re-fails with the same toast. The promised trust prompt never appears.
4. Internally the failure is "Workspace requires trust approval before starting a session." (surfaced verbatim when another session tried send_message to the stuck one).

Why it can never self-resolve (the deadlock)

• The desktop app requires an exact per-path hasTrustDialogAccepted: true entry for the session's cwd.
• The CLI inherits trust from the parent repo directory: running claude (interactive or -p) inside the worktree starts immediately, never shows the folder-trust prompt, and therefore never writes the per-path entry.
• Result: the only flow that writes the entry the app demands is a prompt that will never be shown, because by the CLI's rules the folder is already trusted.

Verified on the affected machine: claude -p "reply OK" in the worktree succeeds with no prompt while the app simultaneously refuses to start a session there.

Workaround

Quit the app, then add the entry manually:

python3 -c "import json,os; p=os.path.expanduser('~/.claude.json'); d=json.load(open(p)); d['projects'].setdefault('<worktree-path>',{})['hasTrustDialogAccepted']=True; json.dump(d,open(p,'w'),indent=2)"

Session starts normally afterwards.

Suggested fixes (either resolves it)

• Desktop app honors ancestor trust the way the CLI does (a worktree under a trusted repo is trusted), or
• The app's "Try again" path shows its own trust dialog when the backing CLI is not going to prompt.

Also worth a look: the toast's wording ("choose Trust workspace when asked") promises a prompt that, in this state, is unreachable.