Expected Behaviour:
Raspberry Pi 5
Debian GNU/ Linux 12 (Bookworm)
Actual Behaviour:
getting error that states it failed to send UDP request, network unreachable
Your debug log shows that you've configured your Pi-hole to use a public DNS server IPv6 as upstream, but your network (or at least your machine hosting Pi-hole) does not have public IPv6 connectivity:
[dns]
upstreams = [
"8.8.8.8",
"8.8.4.4",
"2001:4860:4860:0:0:0:0:8888",
"2001:4860:4860:0:0:0:0:8844"
] ### CHANGED, default = []
*** [ DIAGNOSING ]: Network interfaces and addresses
(…)
2: eth0: <BROADCAST,MULTICAST,UP,LOWER_UP> mtu 1500 qdisc pfifo_fast state UP group default qlen 1000
link/ether <redacted> brd ff:ff:ff:ff:ff:ff
inet 192.168.0.3/24 brd 192.168.0.255 scope global noprefixroute eth0
valid_lft forever preferred_lft forever
inet6 fd80:<redacted>2e/64 scope global dynamic noprefixroute
valid_lft 1779sec preferred_lft 1779sec
inet6 fe80::<redacted>70/64 scope link noprefixroute
valid_lft forever preferred_lft forever
Hence, it can't connect to public IPv6 addresses (range 2000::/3), which triggers the Network Unreachable warning.
To get rid of those warnings, untick Google's IPv6 DNS servers from your Pi-hole's upstreams.