No DNS resolving with "override local DNS" switched on

Tailscale version: 1.20.4 (Mac OS) and 1.22.0 (Linux, Raspberry Pi and Pi-Hole)
Your operating system & version: Mac OS 12.2.1 (Monterey)

I followed the instructions in this guide: Access a Pi-hole or Raspberry Pi from anywhere · Tailscale. I like the idea of having DNS queries being resolved by Pi-Hole no matter to which network I am connected to. However, as soon as I switch on “override local DNS” no DNS resolving is taking place.

; <<>> DiG 9.10.6 <<>>
;; global options: +cmd
;; connection timed out; no servers could be reached
➜  ~ nc -v -z 53
Connection to port 53 [tcp/domain] succeeded!


  • all preferences in the Tailscale client (Mac OS) are set to default (switched on).
  • magic dns is switched on
  • I have entered the IPv4 and the IPv6 address of my Pi-Hole as global name servers
  • in the Pi-Hole settings the interface settings is set to “allow all origins”

Am I doing something wrong or is this a bug? Thanks for your help.

Update. Reinstalled my Raspberry Pi. And now it is working. Apparently something was wrong in my installation. Thanks for rubber ducking :duck: :grinning: