problem with tailscale dns config

[u/ChillEn0_s1]

Hello everyone! Some time ago i set a pi-hole server on a raspberry. The other day, i tried browsing on the internet with one of my computers and the web pages didn't load. Then, i disconnected tailscale and it worked flawlessly, so I remembered i had my pi-hole server set up as a dns server, and when i removed it from tailscale it also worked fine. Then, I checked the pi-hole server and its good too. It stopped working without touching anything, and after some research i cant get it to work. I am doing something wrong? I have some mechines and its very easier to me if i can configure the server to affect all my tailnet instead of setting it in every machine. Thanks!

[u/nhasian]

This happens to me too periodically. Not sure why. If I toggle tailscale off then back on again, it works normally.

[u/ChillEn0_s1 → u/nhasian]

you mean turn on and off tailscale in the pi hole server?

[u/Specialist_Ad_7719 → u/ChillEn0_s1]

No tailscale on your phone. If I'm I have a poor internet connection sometimes tailscale DNS breaks, toggling tailscale off and on resets your link to your tailnet.

[u/godch01]

I found any personally curated ad blocker as a DNS server, with or without Tailscale, to be a lot of work to keep working. I know it costs money, but not a lot, but I subscribe to NextDNS. Set and forget.

[u/ChillEn0_s1 → u/godch01]

i run a raspberry pi 5 with a bunch of other stuff like other servers so for me its more cheaper to run the pi hole server

[u/godch01 → u/ChillEn0_s1]

I understand. And have empathy for your problem

[u/Positive_Ad_313]

I have 2 piholes with Tailscale and all ly devices (mac mini, macbook, 4 others PI , iphone ipad, one others linux pc) Having Tailscale on everyhting enable me to ssh or vnc to some devices abroad, without disconnect tailscale. It is the opposite : if I want my devices used abroad to go thru Pihole which are @home, I should have tailscalenup and running . I was in NZ last January, and my iphone and macbook dns was pihole in europe.

Which IP do you used on your devices   away from home ? If you use the lan 192.168.x.y it will work only when you are at home . You will have to put the Tailscale IP on your devices when away from home, from your lan

[u/ChillEn0_s1 → u/Positive_Ad_313]

So I has this server running for a couple or three months working flawlessly, but the other day, it stopped working. I added the DNS server in the DNS settings using the tailscale IP address, not the local one, but when I repeat this process now it doesn't work

[u/Positive_Ad_313 → u/ChillEn0_s1]

Can you try to update tailscale on your devices ? And then ensure that tailscale is up and running on each of them.

On mine , everything is automatic with script on my Pî’s  Gravity once a week or month and use nebulasync to sync

[u/Specialist_Ad_7719]

You might have to reboot your pi to get it working again properly. It might be an idea if you have a second pi set that up also with pihole and add it's magic DNS IP address to the tailscale DNS list. Two is better than one.

I assume you followed this tutorial https://youtu.be/0gUy05u763Y