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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

** Affects: dnsmasq (Ubuntu)
     Importance: Undecided
         Status: New


** Tags: dnsmasq squid ubuntu xenial
-- 
dnsmasq starts with error on Ubuntu Xenial amd64 when squid installed
https://bugs.launchpad.net/bugs/1761096
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