Tailscale not reconnecting after reboot

What's actually wrong

Tailscale is installed, and 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 itself is fine.

That's not "the VPN is broken." That's unattended start never getting set up.

Checklist: before the next reboot

1. Confirm the box is yours to admin. Shop PC, Pi, NVR/PC — anything you can install software on. Cloud cameras like Ring or Nest are not the right target.
2. Windows: set up unattended Tailscale. Install the official client and sign in once on that machine. Turn on the setting that starts Tailscale before or without an interactive user session (the wording varies by client version — look for "unattended," "start with Windows," or "run as service"). Reboot once on purpose, then confirm from another device that the node is back, without touching the keyboard.
3. Linux: enable the service. After installing and running tailscale up, enable the daemon so it survives a reboot (systemctl enable --now tailscaled, or your distro's equivalent). Reboot once and confirm the node rejoins.
4. Prove it cold. Reboot again, or pull power for 10 seconds. Wait, then check the 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 — that's a different problem (when the box goes dark)
• Shop Wi‑Fi or ISP outages — that's the path, not Tailscale
• Expired auth or a disabled node — just sign in again on the box
• Knowing the box died at all — that's a heartbeat, not a reconnect (email when the box dies)

What you'll write down

Your Tailscale account, your machine's hostname, your login path. No shared secrets from me — the pack has blanks you fill in yourself.