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) -- You received this bug notification because you are a member of Ubuntu Touch seeded packages, which is subscribed to dnsmasq in Ubuntu. https://bugs.launchpad.net/bugs/1761096 Title: dnsmasq starts with error on Ubuntu Xenial amd64 when squid installed Status in dnsmasq package in Ubuntu: Fix Released Status in squid package in Ubuntu: Fix Released Status in dnsmasq source package in Xenial: Confirmed Status in squid source package in Xenial: Confirmed Bug description: Setup to reproduce: Ubuntu Xenial amd64 net install iso from http://archive.ubuntu.com/ubuntu/dists/xenial/main/installer- amd64/current/images/netboot/mini.iso Install system with mostly defaults + LVM + OpenSSH server Note that this bug applies to both DHCP and static IP+DNS network configurations Once server rebooted and is available, log in and install dnsmasq + squid: apt-get update && apt-get install squid dnsmasq output of this can be found at https://pastebin.com/9Atuipju journalctl -xe output at https://pastebin.com/uLhfM4jN Furthermore at this point I can run alternating errors root@ubuntu-min:~# date ; service dnsmasq start ; date Wed Apr 4 09:18:07 CEST 2018 Wed Apr 4 09:18:07 CEST 2018 root@ubuntu-min:~# date ; service dnsmasq stop ; date Wed Apr 4 09:18:39 CEST 2018 Wed Apr 4 09:18:39 CEST 2018 root@ubuntu-min:~# date ; service dnsmasq start ; date Wed Apr 4 09:19:10 CEST 2018 Job for dnsmasq.service failed because a timeout was exceeded. See "systemctl status dnsmasq.service" and "journalctl -xe" for details. Wed Apr 4 09:20:40 CEST 2018 root@ubuntu-min:~# date ; service dnsmasq start ; date Wed Apr 4 09:42:57 CEST 2018 Wed Apr 4 09:42:57 CEST 2018 root@ubuntu-min:~# date ; service dnsmasq stop ; date Wed Apr 4 09:43:14 CEST 2018 Wed Apr 4 09:43:14 CEST 2018 root@ubuntu-min:~# date ; service dnsmasq start ; date Wed Apr 4 09:43:26 CEST 2018 Job for dnsmasq.service failed because a timeout was exceeded. See "systemctl status dnsmasq.service" and "journalctl -xe" for details. Wed Apr 4 09:44:56 CEST 2018 and so on... Each and every 1 out of 2 stop/start cycle fails in 1m30s timeout Complete journalctl -xe output attached To manage notifications about this bug go to: https://bugs.launchpad.net/ubuntu/+source/dnsmasq/+bug/1761096/+subscriptions -- Mailing list: https://launchpad.net/~touch-packages Post to : touch-packages@lists.launchpad.net Unsubscribe : https://launchpad.net/~touch-packages More help : https://help.launchpad.net/ListHelp