Before You Call It Done

Run this end to end from your laptop, with nothing but Tailscale and your key.

1. Tailscale is running
2. ssh yourname@your-server.your-tailnet.ts.net connects
3. claude starts and is signed in
4. Your agent answers a question about your business correctly
5. Reboot the server with sudo reboot, wait two minutes, and confirm all four still work

Why the last one matters

A setup that does not survive a restart is not finished — it is just currently running.

Swap that was never written to /etc/fstab, a service that was never enabled, a mount that only existed in memory: all of these work perfectly until the first reboot, which usually happens weeks later when you have forgotten every detail of how you set it up.

Two minutes now saves a bad afternoon later.

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Server Troubleshooting