My setup was working perfectly for months and months. This is what it is.
T-Mobile 5G Home Internet plugged into an eero.
A Raspberry Pi running Pi Hole and Tailscale installed on the Pi.
I also have various Apple laptops and iOS devices with Tailscale installed.
On my Tailscale admin page I have the DNS directed to the IP address of the Pi Hole shown on the Tailscale admin page.
I could then browse ad free on my iOS devices using the Tailscale VPN.
The DNS of the eero directed to the static IP of the Pi so that everyone on my network got ad blocking automatically.
This setup worked great forever.
A couple of days ago I added a new extender to my eero setup. There were some odd issues that I had and it got sorted out via eero support.
But while on support I heard the tech say he was going to change the DNS address from T-Mobile to Cloudflare. It went over my head but now I realize that he changed the DNS from the IP address of the Pi Hole to Cloudflare.
Yesterday I found this out when I saw some ads on my iPhone in my house.
Tailscale was still working fine at this point.
I changed the DNS on the eero back to my Pi Hole and the network restarted.
Since then my Pi Hole still isn’t automatically blocking ads (it will if you manually change the DNS on the device itself) and Tailscale is now broken.
If I enable the Tailscale VPN on my Mac or iPhone I have no Internet.
I have rebooted the Pi a couple of times.
Tailscale still not working. When I activate it on my Mac or phone I get nothing (although it does show it connects).