[BUG] CoworkVMService 5-second timeout causes persistent "Workspace unavailable" on Windows 11 Pro

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?

Title: CoworkVMService 5-second timeout causes persistent "Workspace unavailable" on Windows 11 Pro
Body:

Environment

Windows 11 Pro
Claude Desktop 1.6608.2.0 (Microsoft Store)
Claude Team plan

Symptom
Cowork shows "Workspace unavailable. The isolated Linux environment failed to start." on every session. Persists across restarts.
Log evidence (%APPDATA%\Claude\logs\cowork_vm_node.log)
Shows consistent 5-second gap between "Configuring Windows VM service..." and "Startup failed: VM service not running" — identical to the pattern documented in #56145 and #48661.
What I've tried

Restarting Claude Desktop and computer
Manually running Start-Service CoworkVMService as Administrator (service shows Running but Claude still fails)
Scheduled task to pre-start service at login (service is Running before Claude opens — still fails)
Waiting 15+ seconds after service starts before opening Claude — still fails

Result: Service runs successfully when started manually but Claude Desktop still cannot connect to it. The "already attempted once" retry guard then blocks all further attempts for the session.
Request: Please extend the 5-second configure timeout and/or add retry-with-backoff as suggested in #56145. Also please investigate why Claude cannot connect to an already-running CoworkVMService.

NOTE: This is Claude generated information as it has been helping me problem solve. I'm not a dev.

What Should Happen?

Cowork Linux sandbox should start successfully and be available for use.

Error Messages/Logs

2026-05-12 09:14:00 [info] [VM:start] Configuring Windows VM service...
2026-05-12 09:14:05 [error] [VM:start] Startup failed: Error: VM service not running. The service failed to start.
2026-05-12 09:14:05 [info] [VM:start] Skipping auto-reinstall (already attempted once)

Steps to Reproduce

1. Open Claude Desktop on Windows 11 Pro
2. Navigate to Cowork tab
3. Sandbox fails immediately with "Workspace unavailable. The isolated Linux environment failed to start."
4. Issue persists across restarts. Manual Start-Service CoworkVMService as Administrator does not resolve it.

Claude Model

Not sure / Multiple models

Is this a regression?

Yes, this worked in a previous version

Last Working Version

_No response_

Claude Code Version

1.6608.2.0 (Claude Desktop / Cowork)

Platform

Other

Operating System

Windows

Terminal/Shell

PowerShell

Additional Information

This issue is related to #56145 and #48661. The 5-second timeout between "Configuring Windows VM service" and failure is consistent across every attempt. Service can be started manually but Claude Desktop still cannot connect to it.