Dispatch: session timeout causes silent message loss (marked "Read" but no response)

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?

Bug Description

When a Dispatch session times out or ends, subsequent messages sent to that Dispatch are marked as "✓ Read" but receive no response whatsoever. There is no error message, no notification that the session has ended, and no prompt to restart. Messages silently disappear.

Steps to Reproduce

1. Open a Dispatch session in the Cowork tab
2. Have a conversation establishing context and tasks
3. Wait for the session to timeout/end (the exact timeout duration is unclear to users)
4. Send new messages to the same Dispatch session
5. Messages are marked "✓ Read" but no response is ever generated

Expected Behavior

At minimum, one of the following should happen:

• A clear notification that the session has ended/timed out when the user sends a new message
• An automatic prompt to restart the session
• A visible indicator showing session status (active / expired)
• The session should attempt to auto-reconnect and process the message

Actual Behavior

• Messages are silently accepted and marked as "✓ Read"
• No response is generated
• No error or timeout notification appears
• User has no way to know the session is dead
• All prior conversation context is lost without warning
• Sending the same message multiple times yields the same silent result

Why This Matters

1. Dispatch is designed for async workflows — users send tasks and check back later, so silent failures are especially deceptive. The "✓ Read" indicator actively misleads the user into thinking the message was received and is being processed.
2. Users build shared context (plans, task assignments, decisions) within a Dispatch session. When the session silently dies, all that context vanishes with no warning.
3. No feedback loop — in my case I sent the same request 3 times over the course of a day, all marked "✓ Read", none processed. I had no way to distinguish "still processing" from "completely dead."

Suggested Fix

When a message is sent to a Dispatch whose backing session has ended, show a clear message like:

"This Dispatch session has ended. Would you like to start a new session? Note: previous conversation context will not be carried over."

This gives the user agency to decide what to do next, rather than waiting indefinitely for a response that will never come.

Environment

• Claude Code Desktop App (macOS)
• macOS Darwin 25.3.0
• Date: 2026-03-29

What Should Happen?

When a message is sent to a Dispatch session whose backing session has ended/timed out, the user should receive a clear notification such as: "This Dispatch session has ended. Would you like to start a new session?" instead of the message being silently marked as "✓ Read" with no response. At minimum, there should be a visible session status indicator (active/expired) so users know whether their messages will be processed.

Error Messages/Logs

No error messages are shown. That is the core problem — messages are silently marked as "Read" with zero feedback or error output.

Steps to Reproduce

1. Open Claude Code Desktop App, go to the Cowork tab
2. Start a new Dispatch session
3. Have a conversation — establish context, discuss plans, assign tasks
4. Leave the session idle for some time (exact timeout unknown, possibly 30-60 minutes)
5. Come back and send a new message to the same Dispatch session
6. Observe: the message is marked "✓ Read" but no response is generated
7. Send the same message again — same result: "✓ Read", no response
8. Repeat — still no response, no error, no timeout notification

Note: This is 100% reproducible. Any Dispatch session that has timed out will silently swallow all subsequent messages.

Claude Model

Opus

Is this a regression?

Yes, this worked in a previous version

Last Working Version

_No response_

Claude Code Version

2.1.87 (Claude Code)

Platform

Anthropic API

Operating System

macOS

Terminal/Shell

Terminal.app (macOS)

Additional Information

_No response_