Hi Alkis,
thank you for your report and your help to make Ubuntu better.
I like your preanalysis and agree to your assumption of some sort of bad 
initialization.

This bug is present in Debian too, and Ubuntu currently doesn't make any 
changes over the Debian package. So this bug would be best fixed directly in 
Debian, and then Ubuntu will pick up the fix automatically.
The only delta you see in Xenial is a security fix, so not a lot of "Ubuntu 
special" that could break it.

Also the versions are pretty much up to date - 2.76 as in Yakkety is the latest 
upstream.
I checked the changelog but there is no mentioning of the issue you are facing, 
yet if easily possible for you it might be worth checking the same on Yakkety 
or even Zesty.

I almost assume that it might be an upstream issue with dnsmasq itself, but in 
that case as well Debian should be notified to be able to pick it up as well.
You clearly have the best setup to reproduce if any more questions come in, 
therefore would you mind filing a bug with Debian and/or upstream and link it 
here please?

** Tags added: needs-upstream-report

-- 
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/1651044

Title:
  ProxyDHCP replies on invalid range

Status in dnsmasq package in Ubuntu:
  New

Bug description:
  In Ubuntu 16.04, I've configured dnsmasq to reply on subnet=10.160.37.0/24, 
yet it replies even when it gets an IP on subnet=10.161.254.0/24.
  I've only seen this after clean system restart. If I restart dnsmasq later 
on, it works as expected.
  Maybe when dnsmasq starts, the network isn't up yet, and it incorrectly 
initializes some networking information? I'm using network-manager with DHCP.

  Details:
  $ egrep -rv '^#|^$' /etc/dnsmasq.*
  /etc/dnsmasq.d/ltsp-server-dnsmasq.conf:dhcp-range=10.160.37.0,proxy
  
/etc/dnsmasq.d/ltsp-server-dnsmasq.conf:dhcp-range=192.168.67.20,192.168.67.250,8h
  /etc/dnsmasq.d/ltsp-server-dnsmasq.conf:enable-tftp
  /etc/dnsmasq.d/ltsp-server-dnsmasq.conf:tftp-root=/var/lib/tftpboot/
  /etc/dnsmasq.d/ltsp-server-dnsmasq.conf:dhcp-option=17,/opt/ltsp/i386
  /etc/dnsmasq.d/ltsp-server-dnsmasq.conf:dhcp-vendorclass=etherboot,Etherboot
  /etc/dnsmasq.d/ltsp-server-dnsmasq.conf:dhcp-vendorclass=pxe,PXEClient
  /etc/dnsmasq.d/ltsp-server-dnsmasq.conf:dhcp-vendorclass=ltsp,"Linux ipconfig"
  
/etc/dnsmasq.d/ltsp-server-dnsmasq.conf:dhcp-boot=net:pxe,/ltsp/i386/pxelinux.0
  
/etc/dnsmasq.d/ltsp-server-dnsmasq.conf:dhcp-boot=net:etherboot,/ltsp/i386/nbi.img
  /etc/dnsmasq.d/ltsp-server-dnsmasq.conf:dhcp-boot=net:ltsp,/ltsp/i386/lts.conf
  /etc/dnsmasq.d/ltsp-server-dnsmasq.conf:dhcp-option=vendor:pxe,6,2b
  /etc/dnsmasq.d/ltsp-server-dnsmasq.conf:dhcp-no-override
  /etc/dnsmasq.d/ltsp-server-dnsmasq.conf:pxe-service=X86PC, "Boot from 
network", /ltsp/i386/pxelinux

  $ ip a
  1: lo: <LOOPBACK,UP,LOWER_UP> mtu 65536 qdisc noqueue state UNKNOWN group 
default qlen 1
      link/loopback 00:00:00:00:00:00 brd 00:00:00:00:00:00
      inet 127.0.0.1/8 scope host lo
         valid_lft forever preferred_lft forever
      inet6 ::1/128 scope host 
         valid_lft forever preferred_lft forever
  2: enp2s0: <BROADCAST,MULTICAST,UP,LOWER_UP> mtu 1500 qdisc pfifo_fast state 
UP group default qlen 1000
      link/ether d0:50:99:a6:bc:0a brd ff:ff:ff:ff:ff:ff
      inet 10.161.254.185/24 brd 10.161.254.255 scope global dynamic enp2s0
         valid_lft 431873sec preferred_lft 431873sec
      inet6 fe80::f363:c1e2:9cb8:d9e2/64 scope link 
         valid_lft forever preferred_lft forever

  $ sudo netstat -nap | grep dnsmasq
  [sudo] password for administrator: 
  tcp        0      0 0.0.0.0:53              0.0.0.0:*               LISTEN    
  843/dnsmasq     
  tcp6       0      0 :::53                   :::*                    LISTEN    
  843/dnsmasq     
  udp        0      0 0.0.0.0:53              0.0.0.0:*                         
  843/dnsmasq     
  udp        0      0 0.0.0.0:67              0.0.0.0:*                         
  843/dnsmasq     
  udp        0      0 0.0.0.0:69              0.0.0.0:*                         
  843/dnsmasq     
  udp        0      0 0.0.0.0:4011            0.0.0.0:*                         
  843/dnsmasq     
  udp6       0      0 :::53                   :::*                              
  843/dnsmasq     
  udp6       0      0 :::69                   :::*                              
  843/dnsmasq     
  unix  2      [ ]         DGRAM                    15746    843/dnsmasq        
 

  $ grep dnsmasq /var/log/syslog | tail -n 30
  Dec 19 10:52:17 ltsp-server systemd[1]: Starting dnsmasq - A lightweight DHCP 
and caching DNS server...
  Dec 19 10:52:17 ltsp-server dnsmasq[630]: dnsmasq: syntax check OK.
  Dec 19 10:52:20 ltsp-server dnsmasq[843]: started, version 2.75 cachesize 150
  Dec 19 10:52:20 ltsp-server dnsmasq[843]: compile time options: IPv6 
GNU-getopt DBus i18n IDN DHCP DHCPv6 no-Lua TFTP conntrack ipset auth DNSSEC 
loop-detect inotify
  Dec 19 10:52:20 ltsp-server dnsmasq[843]: DNS service limited to local subnets
  Dec 19 10:52:20 ltsp-server dnsmasq-dhcp[843]: DHCP, IP range 192.168.67.20 
-- 192.168.67.250, lease time 8h
  Dec 19 10:52:20 ltsp-server dnsmasq-dhcp[843]: DHCP, proxy on subnet 
10.160.37.0
  Dec 19 10:52:20 ltsp-server dnsmasq-tftp[843]: TFTP root is /var/lib/tftpboot/
  Dec 19 10:52:20 ltsp-server dnsmasq[843]: no servers found in 
/var/run/dnsmasq/resolv.conf, will retry
  Dec 19 10:52:20 ltsp-server dnsmasq[843]: read /etc/hosts - 7 addresses
  Dec 19 10:52:23 ltsp-server systemd[1]: Started dnsmasq - A lightweight DHCP 
and caching DNS server.
  Dec 19 10:52:29 ltsp-server dnsmasq[843]: reading /var/run/dnsmasq/resolv.conf
  Dec 19 10:52:29 ltsp-server dnsmasq[843]: ignoring nameserver 127.0.0.1 - 
local interface
  Dec 19 10:52:29 ltsp-server dnsmasq[843]: using nameserver 194.63.238.4#53
  Dec 19 10:52:29 ltsp-server dnsmasq[843]: using nameserver 8.8.8.8#53
  Dec 19 08:52:47 ltsp-server dnsmasq-dhcp[843]: PXE(enp2s0) 52:54:00:8f:74:ad 
proxy
  Dec 19 08:52:47 ltsp-server dnsmasq-dhcp[843]: PXE(enp2s0) 10.161.254.195 
52:54:00:8f:74:ad /ltsp/i386/pxelinux.0
  Dec 19 08:52:47 ltsp-server dnsmasq-tftp[843]: sent 
/var/lib/tftpboot/ltsp/i386/pxelinux.0 to 10.161.254.195
  ...

  
  Note that it replies in "52:54:00:8f:74:ad proxy" while it shouldn't.
  If I run this:
  # service dnsmasq restart

  Then it behaves correctly:
  Dec 19 09:01:17 ltsp-server dnsmasq-dhcp[2381]: no address range available 
for DHCP request via enp2s0

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