The issue I am facing:
When running pihole -up from my server, the upgrade to v6 seems to progress normally, but it hangs when trying to perform DNS resolution. DNS resolution from the local system no longer functions.
Details about my system:
@pi-dns:~# cat /etc/os-release
NAME="Ubuntu"
VERSION="20.04.6 LTS (Focal Fossa)"
ID=ubuntu
ID_LIKE=debian
PRETTY_NAME="Ubuntu 20.04.6 LTS"
@pi-dns:~# ss -tulnp
Netid State Recv-Q Send-Q Local Address:Port Peer Address:Port Process
udp UNCONN 0 0 0.0.0.0:53 0.0.0.0:* users:(("pihole-FTL",pid=757,fd=4))
udp UNCONN 0 0 127.0.0.53:5353 0.0.0.0:* users:(("dnscrypt-proxy",pid=675,fd=6))
udp UNCONN 0 0 [::]:53 [::]:* users:(("pihole-FTL",pid=757,fd=6))
tcp LISTEN 0 1024 0.0.0.0:80 0.0.0.0:* users:(("lighttpd",pid=805,fd=4))
tcp LISTEN 0 32 0.0.0.0:53 0.0.0.0:* users:(("pihole-FTL",pid=757,fd=5))
tcp LISTEN 0 128 0.0.0.0:22 0.0.0.0:* users:(("sshd",pid=759,fd=3))
tcp LISTEN 0 1024 0.0.0.0:443 0.0.0.0:* users:(("lighttpd",pid=805,fd=5))
tcp LISTEN 0 5 127.0.0.1:4711 0.0.0.0:* users:(("pihole-FTL",pid=757,fd=10))
tcp LISTEN 0 4096 127.0.0.53:5353 0.0.0.0:* users:(("dnscrypt-proxy",pid=675,fd=7))
tcp LISTEN 0 1024 [::]:80 [::]:* users:(("lighttpd",pid=805,fd=6))
tcp LISTEN 0 32 [::]:53 [::]:* users:(("pihole-FTL",pid=757,fd=7))
tcp LISTEN 0 128 [::]:22 [::]:* users:(("sshd",pid=759,fd=4))
tcp LISTEN 0 5 [::1]:4711 [::]:* users:(("pihole-FTL",pid=757,fd=11))
The update to v6 seems to set DNSStubListener=no, but it's already disabled prior to the upgrade. There's also no indication that systemd-resolved is in use. The upgrade installer just hangs constantly trying to perform DNS resolution. If I Ctrl-C out of the process and attempt to ping anything, name resolution fails. Ping by IP works fine.
DNS forwarding works Client > pihole > dnscrypt > DNS provider with TLS.
What I have changed since installing Pi-hole:
All systems are operational prior to the attempt to upgrade. I've had to recover the server from backup and started using checkpoints in Hyper-V to test, but I cannot make sense of what's breaking during the upgrade installation.