[BUG] Remote Control fails with generic HTTP 403 when Trusted Devices is enabled (VS Code extension, Windows) instead of the "device not enrolled" error

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?

What's Wrong?

With "Require trusted devices" enabled on my account (Max plan, personal organization), Remote Control fails in the VS Code extension with a generic error:

Remote Control error: Remote Control server rejected the request (HTTP 403) - run /remote-control to retry

The session appears in the session list at claude.ai/code but stays offline (no green dot).

Disabling "Require trusted devices" makes Remote Control work immediately, with no other change. Re-enabling it brings the 403 back.

The documentation describes a dedicated error for this case ("Your organization requires Trusted Devices for Remote Control, but this device is not enrolled") with /login as the fix. That message is never shown. The generic 403 points toward network, proxy or VPN issues, which made this very hard to diagnose.

Re-enrolling does not fix it either.

What Should Happen?

1. If the device is not enrolled, show the documented "device not enrolled" error instead of a generic 403.
2. After /login, the machine should be enrolled and Remote Control should work with Trusted Devices enabled.

Steps to Reproduce

1. On a Max plan, enable "Require trusted devices" in claude.ai account settings.
2. In the VS Code extension on Windows, run /logout, then sign in again.
3. Also sign in through the CLI in a terminal (claude, then /login).
4. Run /remote-control in the VS Code extension.
5. The HTTP 403 error appears and the session stays offline on claude.ai/code and in the mobile app.
6. Disable "Require trusted devices", then run /remote-control again. It now works.

What I already ruled out

• Network: the account was ruled out first, and the issue disappears when the Trusted Devices setting is toggled, with no network change.
• DISABLE_TELEMETRY and DO_NOT_TRACK are not set anywhere (User, Machine and Process environment, ~/.claude/settings*.json, project .claude/settings*.json, VS Code settings).
• Account: /status shows "Claude Max account" with a personal organization. No API key, no ANTHROPIC_BASE_URL, no Bedrock/Vertex.
• Logout/login from the extension: no change.

Environment

• Claude Code: 2.1.289 (VS Code extension, interactive session)
• Platform: Anthropic API (claude.ai subscription, Max)
• OS: Windows 11 Pro 26H2
• VS Code: 1.140.0
• claude --remote-control from a terminal with Trusted Devices enabled: [works / also fails with 403]

Is this a regression?

I don't know.

What Should Happen?

.

Error Messages/Logs

Steps to Reproduce

.

Claude Model

None

Is this a regression?

Yes, this worked in a previous version

Last Working Version

_No response_

Claude Code Version

.

Platform

Anthropic API

Operating System

Windows

Terminal/Shell

Terminal.app (macOS)

Additional Information

_No response_