Tailscale Integration

[yehoshuadimarsky]

First of all, totally love the blog posts on this, and love your approach, thanks so much for teaching and sharing. I have bits and pieces of your setup implemented on my home network but I haven't tied it all together like you have.

I just recently heard about a good VPN company called Tailscale that uses Wireguard under the hood. They have an article about how to integrate that with Pi-Hole. I wonder if/how we could incorporate that into this setup.

I will do some research and see if it's possible, just posting it here to surface the idea and see if you (or anyone else reading this) thought of something.

Thanks.

[yehoshuadimarsky]

Hmm maybe we can use the Tailscale API here https://github.com/tailscale/tailscale/blob/main/api.md

GitHub

tailscale/api.md at main · tailscale/tailscale

The easiest, most secure way to use WireGuard and 2FA. - tailscale/api.md at main · tailscale/tailscale

[benbalter]

Awesome to hear. I've never used Tailscale before personally, but it should work rather well (I know Wireguard is a popular setup to run along side a Pihole and saw many docker-compose examples during my research).

Looking at https://rnorth.org/tailscale-docker/, it seems you'd just add the relevant Tailscale bits to the docker-compose file, ensuring that they share a network interface, and then you can follow the steps in the article you linked to configure Tailscale to use the PiHole for DNS. You may need to modify the docker-compose definition slightly to setup Tailscale as a relay node.

One note, similar to how I'm building Cloudflared from the repo in my own dockerfile, I'd suggest building Tailscale directly from https://github.com/tailscale/tailscale, vs. trusting a third-party to maintain an image.

Using Tailscale with Docker

Richard North's blog

GitHub

GitHub - tailscale/tailscale: The easiest, most secure way to use WireGuard and 2FA.

The easiest, most secure way to use WireGuard and 2FA. - GitHub - tailscale/tailscale: The easiest, most secure way to use WireGuard and 2FA.

[yehoshuadimarsky]

Revisited this after a while, got Tailscale working along with a bunch of stuff: https://github.com/yehoshuadimarsky/pi-hole-cloudflared-docker-compose-ansible-caddy