Cannot reach site via proxy manager

SUPPORT QUESTIONS
1

Running the “offical” Tailscale on Unraid.

I have multiple docker containers running on a Synology NAS. I reach them on my local network via a custom local domain name, rather than IP. For example, I have flame.mydomain.net that gets me to my docker for flame. My process for this is that I set flame.mydomain.net in Pi-Hole local DNS to point to the IP of an Nginx-Proxy-Manager. NPM then sticks the HTTPS on it and forwards to the container IP:Port. Some of my containers require HTTPS, so I just run all local URLS thought this route. Works fine on the local network directly.

However, once I move to the tailnet, they break and I can not figure out where.

I have the following set on my Tailscale container instance: --advertise-exit-node --advertise-routes=10.10.0.0/24,10.10.1.0/24

DNS on Tailscale is set to my Pi-Hole instance with Cloudflare as a secondary.

I swear this used to work, but it has stopped and I can’t seem to find the break point in the Tailnet.

2

Instead of https://flame.mydomain.net, try to use the IP (e.g. https://10.10.0.123) and see if the service behind that IP is reachable this way (after you clicked through the browser’s certificate warning because you didn’t use the domain name).

If that works, then it’s probably a DNS problem.
In that case, on the machine you’re trying to access flame.mydomain.net from, I would try to figure out what exactly is resolving that DNS query and to what IP it’s being resolved, via something like e.g. nslookup or similar.

If it doesn’t get resolved correctly, then you might want to take a look at the DNS settings in the Tailscale admin console.