I believe I was having the same problem, I use the --bind-interfaces option as well as a few --interface options for different interfaces, and dnsmasq would regularly fail to start during boot because one of the interfaces wasn't present yet. Logs show dnsmasq was being started before network.target was reached.
Apr 30 22:23:19 sirius systemd[1]: Starting dnsmasq - A lightweight DHCP and caching DNS server... Apr 30 22:23:20 sirius dnsmasq[1152]: dnsmasq: syntax check OK. Apr 30 22:23:20 sirius dnsmasq[1296]: dnsmasq: unknown interface trunk.3 Apr 30 22:23:20 sirius systemd[1]: dnsmasq.service: Control process exited, code=exited status=2 Apr 30 22:23:20 sirius systemd[1]: Failed to start dnsmasq - A lightweight DHCP and caching DNS server. Apr 30 22:23:20 sirius systemd[1]: dnsmasq.service: Unit entered failed state. Apr 30 22:23:20 sirius systemd[1]: dnsmasq.service: Failed with result 'exit-code'. --- Apr 30 22:23:27 sirius systemd[1]: Reached target Network. I've since added After=network-online.target Wants=network-online.target to the [Unit] section of /lib/systemd/system/dnsmasq.service and restarted once and the problem didn't occur, but this hasn't been extensively tested. -- 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/1531184 Title: dnsmasq doesn't start on boot because its interface isn't up yet Status in dnsmasq package in Ubuntu: Confirmed Bug description: My dnsmasq instance uses "interface=br-vz0" and the interface br-vz0 is managed manually in /etc/network/interfaces. During boot, dnsmasq is started before br-vz0 is created and this causes dnsmasq to exit: Jan 5 08:56:16 simon-laptop dnsmasq[1008]: dnsmasq: unknown interface br-vz0 Jan 5 08:56:16 simon-laptop dnsmasq[1008]: unknown interface br-vz0 Jan 5 08:56:16 simon-laptop dnsmasq[1008]: FAILED to start up Jan 5 08:56:17 simon-laptop NetworkManager[937]: <info> NetworkManager (version 1.0.4) is starting... ... Jan 5 08:56:18 simon-laptop NetworkManager[937]: <info> interface-parser: parsing file /etc/network/interfaces ... Jan 5 08:56:18 simon-laptop NetworkManager[937]: <info> found bridge ports none for br-vz0 Jan 5 08:56:18 simon-laptop NetworkManager[937]: <info> adding bridge port none to eni_ifaces Jan 5 08:56:18 simon-laptop NetworkManager[937]: <info> management mode: unmanaged ProblemType: Bug DistroRelease: Ubuntu 16.04 Package: dnsmasq 2.75-1 ProcVersionSignature: Ubuntu 4.3.0-5.16-generic 4.3.3 Uname: Linux 4.3.0-5-generic x86_64 ApportVersion: 2.19.3-0ubuntu2 Architecture: amd64 CurrentDesktop: Unity Date: Tue Jan 5 09:53:30 2016 PackageArchitecture: all SourcePackage: dnsmasq UpgradeStatus: No upgrade log present (probably fresh install) To manage notifications about this bug go to: https://bugs.launchpad.net/ubuntu/+source/dnsmasq/+bug/1531184/+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