Your debug log shows your main issue to be failing connectivity for both IPv4 and IPv6:
*** [ DIAGNOSING ]: Name resolution (IPv4) using a random blocked domain and a known ad-serving domain
[✗] Failed to resolve on lo (127.0.0.1)
[✗] Failed to resolve on enp3s0 (10.0.0.250)
[✓] doubleclick.com is 142.251.32.78 via a remote, public DNS server (8.8.8.8)
*** [ DIAGNOSING ]: Name resolution (IPv6) using a random blocked domain and a known ad-serving domain
[✗] Failed to resolve on lo (::1)
[✗] Failed to resolve on enp3s0 (2607:<redacted>2d)
[✗] Failed to resolve on enp3s0 (2607:<redacted>ed)
[✗] Failed to resolve on enp3s0 (fe80::<redacted>)
[✓] doubleclick.com is 2607:f8b0:400b:804::200e via a remote, public DNS server (2001:4860:4860::8888)
This usually hints at port 53 not allowed to handle traffic on your host machine.
You should check your Pi-hole host machine's firewall configuration for Pi-hole's required ports.
I also noted that you seem to be using .local
with your domains, e.g.:
-rw-r--r-- 1 root root 75 Jan 8 20:54 /etc/pihole/custom.list
10.0.0.1 router.local
Note that .local
is reserved for mDNS usage and should NOT be used with plain DNS.
Also, your router seems to advertise your ISP's IPv6 DNS servers and its own IPv6 address as DNS servers:
*** [ DIAGNOSING ]: contents of /etc
lrwxrwxrwx 1 root root 39 Aug 9 07:56 /etc/resolv.conf -> ../run/systemd/resolve/stub-resolv.conf
nameserver 2607:f798:18:10:0:640:7125:5204
nameserver 2607:f798:18:10:0:640:7125:5198
nameserver 2607:<redacted>0b
You should check your router's IPv6 DNS configuration.
As your router is advertising alternative DNS resolvers (including its own IPv6 address) as DNS server, that allows your clients to by-pass Pi-hole.
You'd have to find a way to configure your router to advertise your Pi-hole host machine's IPv6 as DNS server or to stop advertising its own.
You'd have to consult your router's documentation sources on further details for its IPv6 configuration options.
If your router doesn't support configuring IPv6 DNS, you could consider disabling IPv6 altogether (unless you depend on it for reasons).
If your router doesn't support that either, your clients will always be able to bypass Pi-hole via IPv6.