[Resolved ]Recent ubuntu update causes strange DNS issue

Sounds a bit like the interface is reported a bit late.
Check dmesg.
Could be driver issue.
Not sure if works but for diagnosing, you could try delay pihole-FTL a bit by editing below file:

sudo nano /etc/init.d/pihole-FTL

And squeeze in a sleep command (30 seconds just to be sure :wink: ) somewhere here:

#!/bin/bash
### BEGIN INIT INFO
# Provides:          pihole-FTL
# Required-Start:    $remote_fs $syslog
# Required-Stop:     $remote_fs $syslog
# Default-Start:     2 3 4 5
# Default-Stop:      0 1 6
# Short-Description: pihole-FTL daemon
# Description:       Enable service provided by pihole-FTL daemon
### END INIT INFO

sleep 30

FTLUSER=pihole
PIDFILE=/var/run/pihole-FTL.pid
[..]
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