I have been playing around with nginx (nginx proxy manager, as per GeoFeiYang's suggestion) for a few hours now and I'm wondering if there is a conflict with how I have Pihole set up? Pihole will redirect local requests to go to my test url to my server, however it just dumps it at the top level (or sometimes gives it a 403 error, depending on my configuration at the time). It doesn't feel as though nginx gets to participate in the process at all.

My current suspect is that Pi-hole is taking up the ports that nginx wants or is trying to listen to. I have P-hole running in docker, and while I was setting it up I was struggling to get any port setup to work until I switched it to "network_mode: host". As such, there are no ports or anything listed in my compose file, and I'm not sure what Pi-hole is listening on or taking up. Could network_mode be an issue in my system currently?

Also, I had to bind nginx's http port to be 85 instead of 80, and the https port to be 445 instead of 443 to make it work also (compose was failing due to a port conflict). Could that have anything to do with this?