I Gave My Dead Raspberry Pi to an AI Agent. It Fixed Everything Over SSH.

A headless Raspberry Pi 4. A failed OS upgrade. No monitor, no keyboard, no network. One AI agent, one Jetson Nano, and a Tailscale connection.

The Situation

I run a headless Raspberry Pi 4 called homepi that handles critical home infrastructure: NextDNS, PiVPN/WireGuard, Tailscale, Docker, and Pi-hole. It sits in a closet with no monitor attached.

Last week, I attempted to upgrade from Raspbian 10 (Buster) to 11 (Bullseye). The apt full-upgrade ran for hours, asked me a few config file questions, then went silent. The Pi never came back to the network.

No DHCP lease. No SSH. No ping. The router showed nothing.