Using Tails with pi-hole

Anyone see any issues with me pointing a computer running Tails to the pi-hole? Tails doesn't seem to do a good job of blocking ads.

Shouldn't be an issue, if you're running Tails for privacy concerns just make sure you trust the upstream DNS server you have set in Pi-hole as they will see the requests that pass through Pi-hole and are resolved upstream.

Okay thanks, think I'm using OpenDNS. I just run Tails occasionally if I want to do some research in privacy. It's too constrictive to run full time as you can't sign into anything without possibly giving yourself away.

If the site your connecting to is HTTPS then it's end to end encrypted and any data in that pipe is protected. Looks to use TOR so your IP just shows as the Tor exit node.

https://caddyserver.com/docs/mitm-detection is a good site to check and see if there are problems anywhere in the chain, as well as https://whoer.net.

Thanks for all of the additional information, I'll definitely take a look.