[BUG] Cowork Dispatch stuck offline on macOS for 3+ days, survives updates and relaunches

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?

The main Cowork Dispatch thread has shown "Desktop appears offline. Will run when it reconnects." continuously for 3+ days as of 22 April 2026. Claude Desktop app is running, Keep awake is enabled, and the machine is awake during the affected window.

This appears to match the pattern in existing open issues:

• #45937 (Dispatch main conversation permanently offline despite working Cowork tasks)
• #49545 (Claude Dispatch permanently showing "desktop appears offline" for multiple weeks)
• #45962 (Dispatch shows "desktop appears offline" on macOS despite app running)

The v1.3109.0 release resolved an earlier incident on 16 April 2026, but my issue began after that release and has persisted through two subsequent app updates and relaunches.

Environment:

• OS: macOS (Apple Silicon)
• Claude Desktop: latest (updated twice during affected window)
• Claude mobile app: latest
• Plan: [Pro / Max — fill in before submitting]
• Feature: Cowork Dispatch

Troubleshooting already attempted:

• Relaunched Claude Desktop twice
• Updated the app twice during the affected window
• Confirmed Keep awake toggle is on
• Confirmed app is running and machine is awake

Impact: Scheduled tasks (Morning inbox digest, Afternoon inbox scan) cannot be verified as executing. Business-critical workflow affected.

Anthropic support Conversation ID: 215474005577618 (AI agent looped through 5 responses without human escalation despite explicit requests).

What Should Happen?

The main Cowork Dispatch thread should recognise the running Claude Desktop app and process messages normally. The "Desktop appears offline" state should not persist when the app is running, the machine is awake, and Keep awake is enabled. Scheduled tasks should execute on their configured schedule and results should be visible in task history.

Error Messages/Logs

No error messages are shown in the UI. The only visible indicator is:

"Desktop appears offline. Will run when it reconnects."

This message is displayed in the main Cowork Dispatch thread regardless of whether the message is sent from desktop, mobile, or web.

Steps to Reproduce

1. Open Claude Desktop on macOS (Apple Silicon, latest version)
2. Ensure Keep awake is toggled on in Cowork Dispatch settings
3. Navigate to Cowork → Dispatch → main Dispatch thread
4. Send any message (e.g. "are you working?")
5. Observe response: "Desktop appears offline. Will run when it reconnects."
6. Relaunch Claude Desktop (Cmd+Q, reopen)
7. Repeat step 4
8. Observe same offline response persists
9. Update Claude Desktop to latest version when update is available
10. Repeat step 4
11. Observe same offline response persists across 3+ days

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

latest

Platform

Anthropic API

Operating System

macOS

Terminal/Shell

Terminal.app (macOS)

Additional Information

This bug is in the Claude Desktop macOS app (Cowork Dispatch feature), not the Claude Code CLI. I am filing here because existing Cowork Dispatch bugs are tracked in this repo (#45937, #49545, #45962). Several fields in this form do not apply to Cowork and have been filled with N/A or best-fit values.