Tailscale hostnames for Pi-hole stats

Tailscale is a fantastic secure mesh VPN that lets you connect all of your devices to each other, no matter where they are or if you've exposed them publicly to the internet. I use it extensively to use all my homelab services and run it on virtually every server. They have a very generous free tier and hope that enthusiasts enjoy it so much that they bring it to their workplace.

Tailscale publishes a great article on how to use a Pi-hole as the DNS server on your tailnet, allowing you to fully control the DNS of your device no matter what network you are connected to while leveraging their Magic DNS to connect to the other devices on your tailnet. One thing it doesn't cover is how to reenable conditional forwarding for your Pi-hole so that your statistics are not full of your Tailscale assigned 100.x.x.x addresses but instead show the machines hostname.

Conditional forwarding

Pi-hole already supports conditional forwarding but the UI only lets you configure a single local network. If you are like me, you still want to get the statistics for your local network but also would like to get the statics for machines on your tailnet. Luckily, Pi-hole uses dnsmasq and it's easy enough to add our own configuration file to support this use case.

Configuration

Pi-hole will load all configuration files for dnsmasq from /etc/dnsmasq.d/. To support looking up the Tailscale hostnames, we need to add our own configuration file to this directory.

rev-server=100.64.0.0/10,100.100.100.100

The IP address range 100.64.0.0/10 comes from the Tailscale documentation. 100.100.100.100 is the IP address of the local Tailscale DNS server. You will see this address if you have MagicDNS enabled, it will be listed as the DNS server for your tailnet.