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

[IP2RG]

Preflight Checklist

• I have searched existing issues and this hasn't been reported yet
• This is a single bug report (please file separate reports for different bugs)
• 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

• Updated Claude Desktop to the latest version
• Fully quit (Cmd+Q) and relaunched the app
• Logged out and logged back in
• Clicked Retry multiple times
• 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

[ted8008208820-oss]

I'm having the same issue. When I clear the Cowork Dispatch Session and try to recreate it, I keep getting a “retry” prompt.

[jlopezg191]

Having same issue, any updates?

[IP2RG]

It works now. I opened Dispatch on both my desktop and the Claude app on my iPhone simultaneously. It seems there’s some synchronization mechanism that restored normal behavior.

[Atrevinom]

When can we expect a fix to this?

[wv-jessejjohnson]

Same issue for me as well. Glad to see I'm not the only one.

Following this comment fix the issue for me.

[micheleokimura]

Confirming this bug on macOS, Max plan — persistent for 10+ days.

Specific failure state from client logs:

• Stale session ID pinned in client: session_01Dq7FgHn86hmgZxZonoQWbF
• This session fails ReconnectSession with Session not found (HTTP 400) on every single app launch since 2026-04-15
• Log line example: [sessions-bridge] Failed to reconnect session session_01Dq7FgHn86hmgZxZonoQWbF: ReconnectSession: Failed with status 400: Invalid request: Session not found
• Dispatch endpoint returned intermittent 503 overloaded_error on /v1/sessions?tags=cowork-dispatch-local around 2026-04-22, but failure is persistent (not transient overload).

Secondary symptom on the same account:

• Persistent 404s on /api/organizations/[org-id]/model_configs/claude-opus-4-7[1m] — note the bracketed [1m] suffix, looks like a malformed model identifier.

Client-side reset already performed (nothing worked):

• Uninstall + reinstall Claude.app (current: /Applications/Claude.app, auto-updates confirmed via Sparkle/ShipIt)
• Log out / log back in
• Multiple full system restarts
• Moved to backup + relaunched fresh: IndexedDB/, Local Storage/, Session Storage/, Cookies, Cookies-journal, and ~/Library/Preferences/com.anthropic.claudefordesktop.plist

After full client-state reset the Dispatch UI still displays "Session couldn't be created." Behavior is identical before and after.

Confirmed account-specific: verified with 10+ contacts on Mac and PC that Dispatch works normally on their accounts.

Support channel status: email support unresponsive for the duration.

Requesting routing to the Cowork/Dispatch engineering team. Org ID available on request — happy to provide privately.

[github-actions]

Closing for now — inactive for too long. Please open a new issue if this is still relevant.

[KENNE1982]

Me too