Tailscale not reconnecting after reboot

What’s actually wrong

Tailscale is installed. It worked yesterday. After a reboot it sits quiet until someone signs into the desktop or re-runs the client. Remote access is gone even though the machine is fine.

That’s not “VPN is broken.” That’s unattended start never got set.

Checklist: before the next reboot

1. Confirm the box is yours to admin. Shop PC, Pi, NVR/PC you can install software on. Cloud cameras (Ring, Nest, etc.) are not the box (wrong target).
2. Windows: unattended Tailscale. Install the official client. Sign in once on that machine. Turn on the setting that starts Tailscale before / without an interactive user session (wording varies by client version; look for unattended / start with Windows / run as service). Reboot once on purpose. From another device, confirm the node is back without touching the keyboard.
3. Linux: enable the service. After install and tailscale up, enable the daemon so it survives reboot (systemctl enable --now tailscaled or your distro’s equivalent). Reboot once. Confirm the node rejoins.
4. Prove it cold. Reboot again (or pull power for 10 seconds). Wait. Check Tailscale admin from your phone. If it’s offline until you log in locally, unattended still isn’t done.
5. Write the break-glass note. Where the machine is, who can touch it, what “signed in once” looked like. Future-you at 11 p.m. will thank you.

What this does not fix

• Dead hardware or a full disk: different problem (when the box goes dark)
• Shop Wi‑Fi / ISP outages: the path, not Tailscale
• Auth that expired or a disabled node: sign in again on the box
• Email when the box dies: that’s a heartbeat, not reconnect (email when the box dies)

Placeholders you’ll fill in

Your Tailscale account. Your machine hostname. Your login path. No shared secrets from me. The pack uses blanks you own.