I confirm that every second 
 $ systemctl restart dnsmasq
hangs

Also I confirm that removing squid resolved the situation.

I found that it does this:
1. /bin/sh /etc/init.d/dnsmasq systemd-stop-resolvconf
2. /bin/sh /etc/init.d/dnsmasq systemd-start-resolvconf

Both will call hooks like:

0     0 11642 11634  20   0   4364   660 wait   S    ?          0:00  \_ 
run-parts --arg=-a --arg=lo.dnsmasq /etc/resolvconf/update.d
0     0 11659 11642  20   0   4364   664 wait   S    ?          0:00      \_ 
run-parts /etc/resolvconf/update-libc.d
0     0 11672 11659  20   0   4504   704 wait   S    ?          0:00          
\_ /bin/sh /etc/resolvconf/update-libc.d/squid
0     0 11673 11672  20   0   4504  1648 wait   S    ?          0:00            
  \_ /bin/sh /usr/sbin/invoke-rc.d squid reload
4     0 11691 11673  20   0  24888  1388 poll_s S    ?          0:00            
      \_ systemctl reload squid.service


This is what actually times out - the squid hook.

The "systemctl reload squid.service" call seems to take too long every
second time?!

A single "systemctl reload squid.service" for these seems to take ~100 seconds 
for me.
OTOH a direct call to it is fast every time.

This needs to be debugged in detail, but seems well reproducible.


** Also affects: dnsmasq (Ubuntu Xenial)
   Importance: Undecided
       Status: New

** Changed in: dnsmasq (Ubuntu Xenial)
       Status: New => Confirmed

** Changed in: dnsmasq (Ubuntu)
       Status: New => Fix Released

** Changed in: dnsmasq (Ubuntu Xenial)
   Importance: Undecided => High

** Tags added: server-next

** Also affects: squid (Ubuntu)
   Importance: Undecided
       Status: New

** Changed in: squid (Ubuntu Xenial)
       Status: New => Confirmed

** Changed in: squid (Ubuntu Xenial)
   Importance: Undecided => High

** Changed in: squid (Ubuntu)
       Status: New => Fix Released

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Matching subscriptions: Ubuntu 16.04 Bugs
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

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