[BUG] [Cowork Dispatch] Stuck in infinite "Could not process image" retry loop — no way to recover without data wipe

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?

Cowork Dispatch gets stuck in an unrecoverable infinite retry loop when it fails to process image attachments. The API repeatedly returns 400 invalid_request_error: "Could not process image" and Dispatch keeps retrying the same request indefinitely. Since Dispatch is a single continuous thread with no way to start a new session, and the images are baked into the conversation context, every subsequent message re-triggers the error loop.

What Should Happen?

Dispatch should implement a retry limit (e.g. 3 attempts) before giving up on image processing
After hitting a persistent error, Dispatch should surface the error to the user and continue accepting new messages normally
Users should have a way to delete specific messages/attachments from the Dispatch thread, or at minimum clear the current task context
User commands like "stop" or "cancel" should interrupt the retry loop

Error Output
json{
"type": "error",
"error": {
"type": "invalid_request_error",
"message": "Could not process image"
},
"request_id": "req_011CZMXWC9PzPAzWKrQP4efX"
}
Multiple unique request IDs observed, confirming repeated retry attempts:

req_011CZMXWC9PzPAzWKrQP4efX
req_011CZMXY4S77nXZoSPzLo2Vm
req_011CZMXcUS6nSqpubrHtMVnx

Impact

Severity: Critical — Dispatch is completely unusable with no recovery path short of wiping app data
Data loss risk: The only documented workaround (wiping ~/Library/Application Support/Claude/) destroys all Cowork conversation history permanently
Workaround: Fall back to regular Cowork (non-Dispatch) for new tasks

Environment

Claude Desktop: latest version
OS: macOS 26.2 (25C56), MacBook Air 13-inch M4, 24GB RAM
Plan: Max
Feature: Cowork Dispatch (research preview)

Related Issues

#7122 — Same "Could not process image" infinite loop in Claude Code CLI (closed as duplicate)
#36157 — Dispatch causes black screen freeze, requires full data wipe to recover

Error Messages/Logs

API Error: 400 {"type":"error","error":{"type":"invalid_request_error","message":"Could not process image"},"request_id":"req_011CZMXWC9PzPAzWKrQP4efX"}

Steps to Reproduce

Steps to Reproduce

Open Cowork → Dispatch
Send a message with multiple screenshot attachments (in my case, 5 PNG screenshots as reference designs)
Dispatch attempts to process the images and hits the API error
Error repeats indefinitely: API Error: 400 {"type":"error","error":{"type":"invalid_request_error","message":"Could not process image"},"request_id":"req_011CZMXWC9PzPAzWKrQP4efX"}
Sending new messages (e.g. "stop", "abort", "ignore the images") does not break the loop — the error continues
Force-quitting and relaunching Claude Desktop does not resolve it — the loop resumes on relaunch

Claude Model

Not sure / Multiple models

Is this a regression?

I don't know

Last Working Version

_No response_

Claude Code Version

Clude for Mac version 1.1.8359

Platform

Anthropic API

Operating System

macOS

Terminal/Shell

Terminal.app (macOS)

Additional Information

_No response_