[BUG] Cowork Dispatch — "Session couldn't be created" on macOS (Pro Plan)

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?

When clicking Dispatch in the Cowork sidebar, the session fails immediately with the error:

"Session couldn't be created."

A "Retry" button is shown, but clicking it produces the same result. The session never initializes.

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Environment

• OS: macOS (Apple Silicon)
• App: Claude Desktop (latest version, updated via Help → Check for Updates)
• Plan: Pro
• Feature: Cowork → Dispatch (research preview)

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Troubleshooting Already Attempted

• [x] Updated Claude Desktop to the latest version
• [x] Fully quit (Cmd+Q) and relaunched the app
• [x] Logged out and logged back in
• [x] Clicked Retry multiple times
• [x] Standard Cowork sessions work normally — issue is isolated to Dispatch

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Additional Context

This appears related to the known macOS entitlement issue (com.apple.vm.networking missing from app signature) reported in #40283, which prevents the internal VM from establishing a network connection. The Dispatch session never reaches a live state as a result.

Referencing related issues: #40283, #40178, #40142, #37713

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What Should Happen?

Expected Behavior

Clicking Dispatch should initialize a session and allow task dispatching as intended.

Error Messages/Logs

**Actual Behavior**

Session initialization fails immediately. No session is created. The error persists after retrying.

Steps to Reproduce

Steps to Reproduce

1. Open Claude Desktop on macOS
2. Navigate to Cowork (top center tab)
3. Click Dispatch in the left sidebar
4. Observe: error message "Session couldn't be created." appears with a Retry button
5. Click Retry → same error repeats

Reproducibility: 100% — consistent across all attempts

Claude Model

None

Is this a regression?

No, this never worked

Last Working Version

_No response_

Claude Code Version

unknown

Platform

Anthropic API

Operating System

macOS

Terminal/Shell

Terminal.app (macOS)

Additional Information

Screenshots
<img width="2060" height="670" alt="Image" src="https://github.com/user-attachments/assets/b3410c7c-37a4-46bc-a065-61c79a1be220" />

<img width="1938" height="884" alt="Image" src="https://github.com/user-attachments/assets/3cf79aeb-de28-43cb-b26b-96f171791f44" />