ChickenBoo

You can do the basic records via file. /etc/pihole/custom.list is a hosts formatted file for records so you don’t have to use a gui.

I had dns issues until I got my allowed ips squared away. You could try setting it to 0.0.0.0/0 if it’s not already to verify it’s not the problem.

The lines before it seem to imply you’ve run it before. If this is a new install I’d try dropping the scheme entirely and starting again.

I use this guy https://github.com/haugene/docker-transmission-openvpn

Open up the transmission rpc port and you’re golden. It also sets up a proxy for any other services/devices you want to run through the VPN. Supports port forwarding for PIA too.

I’ve had good luck with whisk.com.

Even if your router can issue two DNS servers you shouldn’t add a second that’s not a pihole.

Otherwise a client will just fail over any blocked lookups to the secondary, negating the purpose of a pihole.

I found it easiest to get them running on docker. The documentation wasn’t FANTASTIC, but it got me there in the end.

Then I have nginx proxy manager running in another docker container, which handles the virtual hosts for me. It’s the one actually bound to 80 and 443. Will help you get set up with SSL certs easily, too.