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. I pulled the 32GB SanDisk microSD card and plugged it into my Mac. Finder showed only the FAT32 /boot partition. The ext4 root partition — where all the configs and logs live — was invisible to macOS. This is where most people would reach for a fresh SD card and start over. But I had an AI agent, and I wanted to see how far it could go.…