
After 3 days of countless attempts to resolve Failed to start Claude’s workspace, VM connection timeout after 60 seconds, I finally found a fix. Came across via GitHub, and I’ll share the steps below:
Fix: Cowork VM stuck at guest_vsock_connect (macOS 26.x)
If Cowork fails to start with the VM timing out at the guest_vsock_connect step, resetting the VM bundle fixes it:
1. Fully quit Claude Desktop (Cmd+Q, may need twice)
2. Verify it’s dead
ps aux | grep -i Claude.app | grep -v grep
3. (Optional) Back up session data if you want to preserve it
mkdir -p ~/Documents/claude-vm-backup
cp ~/Library/Application\ Support/Claude/vm_bundles/claudevm.bundle/sessiondata.img ~/Documents/claude-vm-backup/
cp ~/Library/Application\ Support/Claude/vm_bundles/claudevm.bundle/macAddress ~/Documents/claude-vm-backup/
cp ~/Library/Application\ Support/Claude/vm_bundles/claudevm.bundle/machineIdentifier ~/Documents/claude-vm-backup/
4. Delete the VM bundle
rm -rf ~/Library/Application\ Support/Claude/vm_bundles/
5. Relaunch Claude Desktop - it will re-download the VM image (~10 GB)
First launch may take a few minutes. Cowork conversations are NOT lost (stored separately in local-agent-mode-sessions/).
What you lose: In-VM session state (installed packages, files created within Cowork sessions).
What you keep: All Cowork conversation histories, Claude Desktop settings.
As it mentions above, it’s a good idea to backup and be somewhere with fast internet to download the 10 gigs.
Building a mini app that includes custom surveys, data rooms, and shared spaces for builders and agents. The stack is Vercel + Supabase + Google Cloud + Next.js. Hoping to wrap by Sunday.. and if time allows it, squeeeeeze enrichment into both the survey flow and hangout rooms. Some PMM friends are bypassing customer development interviews or surveys and sticking with AI research. It’s a big no from me dog. Talk to the people, use the intuition, and of course use lord gpt. and why am i building this thing? Because it sounds fun.. And Google Forms + Airtable feel dated. Agent surveys are top of mind.
For here on kenny.is, I rebuilt almost everything without using Figma and it shows. It’s irking.. but I’d rather ship new product, versus PMM this website. websites will turn into containers, anyways, right?