Tailboot – A bootable that connects to your Tailscale network

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Hi everyone, I often use coding agents to debug remote machines when the host OS isn’t working. I built Tailboot for that workflow: it’s a minimal Debian-based live image that boots from USB, joins your tailnet using a Tailscale auth key, and starts Tailscale SSH. It's a minimal image (since you're expected to be connected to the internet), but it's enough to let an agent connect to it over Tailscale SSH and debug issues The access key is injected into the ISO entirely client side, But I generally recommend adding a tag to it that will block it from being able to access other nodes on your network. Github: https://github.com/ShoeBoom/tailboot

Visit product View on Hacker NewsSep 11, 2026

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Indie HackersIH features products with proven revenue · Missing: supports, reddit linkedin, podcasting

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