This is great! I was just looking into buying some hardware for a Pi-hole but this is a much easier way to try it out. I think you can solve this limitation by

This is great! I was just looking into buying some hardware for a Pi-hole but this is a much easier way to try it out. I think you can solve this limitation by passing in a static machine key. Redeploying or upgrading Pi-hole leads to a new Fly.io instance, with a new TailScale private IP, thus requiring an update to the DNS configuration. This is rare enough for me as to be a non-issue, but it might be quite annoying for very frequent travelers. It is stored in a json in /var/lib/tailscale/tailscaled.state. It's a bit off the beaten path but I believe that'll make the new instance keep the same 100.x IP address.