Hello All.

I'm trying to set up pihole and tailscale and get them to play nicely.

My Unraid on the lan is 192.168.1.195. My pihole is br:custom 192.168.1.213 . My router is 192.168.1.1 .
Ideally I'd like my unraid to use the pihole for DNS - My router is configured to use 192.168.1.213 for DNS
So here's where I'm at a loss for settings wise. I have to have something wrong or the wrong combination:
 

Tailscale Outbound Networking: Use Tailscale Subnets & Use Tailscale DNS Settings. 
Then on the Tailscale Admin: DNS setings: Global NameServers: (Override Local DNS? Use Magic DNS? )

The problem I'm having is with every combination I've tried (I'm hopefully missing one that someone knows and it's sobvious to an expert):

DNS won't resolve remotely when connected to tailscale.  From a remote machine, Nslookup - <Enter> and searching for DNS doesn't resolve, and shows my name server as 100.100.100.100.
When I finally DID get it to resolve - if I recall it waws when I enabled use tailscale subnets and use tailscale DNS Settings (on the Unraid -> Settings -> Tailscale -> Advanced Settings), I 'lost' access to 192.168.1.195 on the LAN - I could then only access my unraid on the LAN if I had tailscale installed and used the 100.x private IP.

 

Any hints MUCH appreciated.

Thanks

the main problem you have is called "chicken & egg". To be short, you can use pihole ON Unraid, but not FOR Unraid.

Using it for your router is also delicate, it might work sometimes.

The problem is that dockers on Unraid are started last and only if the array is up and running.

DNS is a basic thing, already needed at boot time.

There will be massive delays, timeouts and unpredictable results if you try to boot up and Pihole is not running yet. Most of them maybe harmless timeouts, but some may also lead to major disfunctions. As I said: UNPREDICTABLE.

 

The best solution would be to get a real Pi and put Pihole onto it, running all the time.

(this is also the next and next-next solution, because every try to run it on Uraid will fail).

It MAY be possible to install Python and Pihole not as a docker but as a native service on UNRAID. This would be started quite early. But I have not heard about anybody that took this complicated way.

 

I set unraid network settings to be 8.8.8.8 and 4.2.2.2 and still seeing the same symptoms...

What I don't get is why unraid starts becoming unresponsive on the LAN IP...?