This is complicated indeed. I also spotted this in the logs during the long
wait:
Oct 25 21:16:07 xenial-squid-dnsmasq systemd[1]: nss-lookup.target: Job
nss-lookup.target/start failed with result 'dependency'.
and nss-lookup.target has something related to dnsmasq:
root@xenial-squid-dnsmasq:~# systemctl status nss-lookup.target
● nss-lookup.target - Host and Network Name Lookups
Loaded: loaded (/etc/insserv.conf.d/dnsmasq; static; vendor preset: enabled)
Drop-In: /run/systemd/generator/nss-lookup.target.d
└─50-hard-dependency-dnsmasq-$named.conf
Active: active since Thu 2018-10-25 21:19:41 UTC; 53s ago
Docs: man:systemd.special(7)
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https://bugs.launchpad.net/bugs/1761096
Title:
dnsmasq starts with error on Ubuntu Xenial amd64 when squid installed
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