Phone device-card sessions never reach desktop after 1.22209 auto-update - env registration 409-conflicts with the app's own Cowork agent (enclave key unavailable)

Bug report: Phone "device card" sessions never reach desktop after 1.22209 auto-update — environment registration 409-conflicts with the app's own Cowork agent

Environment

• App: Claude Desktop for Windows (Microsoft Store / MSIX), 1.22209.0.0 — auto-updated from 1.21459.0.0 on 2026-07-18 ~10:48 KST (this update is when the breakage started)
• Claude Code binary: 2.1.209
• OS: Windows 10 Pro for Workstations 10.0.19045
• Hostname: DESKTOP-C6TNSD3
• Plan: Max (personal account)

Summary

Since the 1.22209 auto-update, creating a new session from the phone's device card (Claude iOS app → 코드 tab → device card "DESKTOP-C6TNSD3") hangs forever at "Allocating sandbox". The request never reaches the desktop (no Poll received work in main.log).

Root cause visible in logs: the desktop's sessions-bridge cannot register its environment — the server rejects every fresh registration with:

[error] [sessions-bridge] Registration conflict (409): Registration: Conflict (409):
A Cowork agent is already registered on DESKTOP-C6TNSD3.
Disconnect it there before registering this device.

…while the "already registered Cowork agent" is this same machine's own registration (apparently stale server-side state from before/during the update). Crucially, every registration attempt is immediately preceded by:

[warn] [device-registry] enclave key unavailable — refusing to resolve row-PK

so the app seemingly cannot prove it is the same device that owns the existing Cowork agent registration, and the server treats it as a stranger claiming an occupied hostname. There is no user-facing way to clear the stale registration (checked claude.ai web settings and the desktop app settings — no device management UI; the 발송 toggle cycle does not clear it).

Request IDs (three failed registration attempts, 2026-07-18 KST)

• 11:51:05 — req_011Cd8mG9xktigbujNF5VQ4n
• 11:59:56 — req_011Cd8mwGAQY5ruhV7xTnrGJ
• 12:04:31 — req_011Cd8nHZS2tfmTjJuyfh1WX

Timeline (2026-07-18, KST)

| Time | Event |
|------|-------|
| ~10:48 | Store auto-update 1.21459 → 1.22209 kills all running sessions ('Utility' process exited with 'killed', Claude Code process exited with code 1) |
| 10:52+ | App relaunches; environment registration succeeds only in reuse mode (Registering environment (reusing env_01Peyyck4Hj4gs4RWbF6PHw9)); persisted remote-control session reconnects fine, but new phone-initiated sessions never arrive |
| 11:13, 11:27, ~11:52, ~12:01 | Phone device-card new sessions all stall at "Allocating sandbox"; desktop log shows zero incoming work for them |
| 11:45 | Removed bridge-state.json (real path under MSIX virtualization: %LOCALAPPDATA%\Packages\Claude_pzs8sxrjxfjjc\LocalCache\Roaming\Claude\) to force fresh registration |
| 11:51:05 | Registering environment (fresh)... → 409 conflict (first request-id above), preceded by the enclave-key warning |
| 11:59, 12:04 | 협업 → "발송" toggle off/on cycles re-init the bridge → same 409 each time |
| ~12:10 | Workaround confirmed: restoring environmentId into bridge-state.json → reuse-mode registration succeeds → phone sessions created via direct URL https://claude.ai/code?environment=env_01Peyyck4Hj4gs4RWbF6PHw9 DO reach the machine and work end-to-end |

What was ruled out

• App restart, full quit + relaunch (multiple times) — no change
• Machine power-cycle — no change
• Clearing bridge-state.json for a fresh environment — blocked by the 409
• 협업 settings: "발송" off/on cycle, "클라우드에서 새 작업 실행" off — no change
• claude.ai web settings (Claude Code / 협업 sections) — no device-deregistration UI exists

What still works (so the breakage is specifically the Cowork device-card dispatch + fresh env registration)

• Desktop-initiated sessions with the 원격 제어 toggle: fully functional
• Opening existing sessions from the phone's session list: fully functional
• Direct-URL new sessions on the reused environment (claude.ai/code?environment=env_01Peyyck4Hj4gs4RWbF6PHw9): fully functional
• The Cowork device DO-bridge itself connects and authenticates ([remote-tools-device] authenticated, device shows 활성 on the phone) — which makes the device card look alive while its sessions go nowhere

Requests

1. Clear (or make user-clearable) the stale server-side Cowork agent registration for this hostname, so fresh environment registration stops 409-ing.
2. Investigate [device-registry] enclave key unavailable — refusing to resolve row-PK on Windows 10 (10.0.19045) after the 1.22209 MSIX update — it appears to be why the device cannot re-claim its own registration.
3. Consider a UI for viewing/removing device & environment registrations (ghost environments have been accumulating for a while and are not deletable from web or phone).