@jakesmolka if you’re *only* accessing that reverse proxy while tailscale is running, assuming you have a domain name/DNS control, just create an entry pointing to the tailscale IP of that reverse proxy. I do that and then also run pi-hole as an “internal” dns with hostnames that point to the non-tailscale IP of the proxy server. No idea if this is the right way to do it but it’s been working great for me and I have no ports opened to the outside world on my router.