Getting this after pihole status and in the web page
DNS service NOT running
Update: If I run pihole -r repair it will run again but after the next reboot it will be broken again.
This is Ubuntu 16.04 LTS on an Intel NUC, new install. I've put in some other utilities like OpenVPN but nothing that should be interacting with dsnmasq that I know of. Prior to this I put PiHole on three other Raspberry Pi3 and worked great so I've used it before (and donated). Still using one as my secondary DNS for this network if this has trouble, which seems it is.
---=== Your debug token is : 0fah9bqn87 Please make a note of it. ===---
sudo dnsmasq --test
dnsmasq: syntax check OK.
systemctl -i status dnsmasq
● dnsmasq.service - dnsmasq - A lightweight DHCP and caching DNS server
Loaded: loaded (/lib/systemd/system/dnsmasq.service; enabled; vendor preset: enabled)
Drop-In: /run/systemd/generator/dnsmasq.service.d
└─50-dnsmasq-$named.conf, 50-insserv.conf-$named.conf
Active: failed (Result: exit-code) since Sun 2017-10-22 10:47:30 EDT; 27min ago
Process: 1142 ExecStart=/etc/init.d/dnsmasq systemd-exec (code=exited, status=2)
Process: 1095 ExecStartPre=/usr/sbin/dnsmasq --test (code=exited, status=0/SUCCESS)
Oct 22 10:47:30 ubuntuserver systemd[1]: Starting dnsmasq - A lightweight DHCP and caching DNS server...
Oct 22 10:47:30 ubuntuserver dnsmasq[1095]: dnsmasq: syntax check OK.
Oct 22 10:47:30 ubuntuserver dnsmasq[1142]: dnsmasq: unknown interface enp3s0
Oct 22 10:47:30 ubuntuserver systemd[1]: dnsmasq.service: Control process exited, code=exited status=2
Oct 22 10:47:30 ubuntuserver systemd[1]: Failed to start dnsmasq - A lightweight DHCP and caching DNS server.
Oct 22 10:47:30 ubuntuserver systemd[1]: dnsmasq.service: Unit entered failed state.
Oct 22 10:47:30 ubuntuserver systemd[1]: dnsmasq.service: Failed with result 'exit-code'.
tail -f /var/log/pihole.log
Oct 22 10:45:52 dnsmasq[31815]: query[A] api.segment.io from 10.0.1.138
Oct 22 10:45:52 dnsmasq[31815]: /etc/pihole/gravity.list api.segment.io is 10.0.1.6
Oct 22 10:46:10 dnsmasq[31815]: query[AAAA] 1.ubnt.pool.ntp.org from 10.0.1.5
Oct 22 10:46:10 dnsmasq[31815]: cached 1.ubnt.pool.ntp.org is NODATA-IPv6
Oct 22 10:46:40 dnsmasq[31815]: query[A] ssl.google-analytics.com from 10.0.1.57
Oct 22 10:46:40 dnsmasq[31815]: /etc/pihole/gravity.list ssl.google-analytics.com is 10.0.1.6
Oct 22 10:46:46 dnsmasq[31815]: query[SOA] local from 10.0.1.6
Oct 22 10:46:46 dnsmasq[31815]: forwarded local to 208.67.222.222
Oct 22 10:46:46 dnsmasq[31815]: forwarded local to 8.8.4.4
Oct 22 10:46:46 dnsmasq[31815]: exiting on receipt of SIGTERM
I will look at this closer tonight but what I'm seeing in the logs is highlighted above, it can't find enp3s0 which I told it to look for in pihole setup and I do have enp3s0 according to ifconfig.
First off, very important note, this is not raspbian. This is regular Ubuntu 16.04 LTS running on an Intel NUC.
After reading some of the things you linked I changed the USB net by mac rules which didn't work. BUT if you read the notes at the top of the page that only applies to network adapters over USB which is NOT what I have.
So at the moment PiHole works for me if I repair the install after rebooting but it will break with each reboot so something is breaking / setting not being retained somewhere.
Experiencing same problem here. dnsmasq.service doesn't start properly on reboot. If started manually after reboot, runs fine. Problem seems to be that it won't start before network adapter is in a ready state.
Edited to add: Web interface starts, and pihole can be enabled from the web interface. Problem is limited to dnsmasq package failing to start at boot. Ubuntu server 16.04