Ubuntu: does not start after reboot

[Hobbabobba]

Expected Behaviour:

after i reboot the the system, i can still use pi-hole. my other computers will still open pages on www.

Actual Behaviour:

URLs are not resolved. I always need to install pi-hole again to get it working. Until the next reboot.
I use Ubuntu on an Orange Pi PC. (When I install pi-hole inside of a Ubuntu 14 VM on ESXi, it does not to be installed again after a reboot)

[Hobbabobba]

ok, found a fix. When i enter

sudo service dnsmasq restart

right after a reboot, it works! Is there a noob-friendly way to automate it?

[PromoFaux]

This may be related to an issue we saw in the past with Ubuntu Mate..

I'm guessing that is what you are using?

It has to do with the interface having an arbitrary name, which is not set until the interfaces service is started. On Ubuntu mate, this happens to be started after dnsmasq. Dnsmasq initially fails because it cannot find the interface named in /etc/dnsmasq/01-pihole.conf

Could you paste in the output of:
cat /etc/dnsmasq/01-pihole.conf please?

[PromoFaux]

here is the thread on reddit about it

[Hobbabobba]

There is no file of this kind, but there is a config-file /etc/dnsmasq.d/01-pihole.conf

# Pi-hole: A black hole for Internet advertisements
# (c) 2015, 2016 by Jacob Salmela
# Network-wide ad blocking via your Raspberry Pi
# http://pi-hole.net
# dnsmasq config for Pi-hole
#
# Pi-hole is free software: you can redistribute it and/or modify
# it under the terms of the GNU General Public License as published by
# the Free Software Foundation, either version 2 of the License, or
# (at your option) any later version.

# If you want dnsmasq to read another file, as well as /etc/hosts, use
# this.
addn-hosts=/etc/pihole/gravity.list

# The following two options make you a better netizen, since they
# tell dnsmasq to filter out queries which the public DNS cannot
# answer, and which load the servers (especially the root servers)
# unnecessarily. If you have a dial-on-demand link they also stop
# these requests from bringing up the link unnecessarily.

# Never forward plain names (without a dot or domain part)
domain-needed
# Never forward addresses in the non-routed address spaces.
bogus-priv

# If you don't want dnsmasq to read /etc/resolv.conf or any other
# file, getting its servers from this file instead (see below), then
# uncomment this.
no-resolv

# Add other name servers here, with domain specs if they are for
# non-public domains.
server=208.67.222.123
server=208.67.220.123

# If you want dnsmasq to listen for DHCP and DNS requests only on
# specified interfaces (and the loopback) give the name of the
# interface (eg eth0) here.
# interface=eth0
# Or which to listen on by address (remember to include 127.0.0.1 if
# you use this.)
# listen-address=127.0.0.1

# Set the cachesize here.
cache-size=10000

# For debugging purposes, log each DNS query as it passes through
# dnsmasq.
log-queries
log-facility=/var/log/pihole.log

# Normally responses which come from /etc/hosts and the DHCP lease
# file have Time-To-Live set as zero, which conventionally means
# do not cache further. If you are happy to trade lower load on the
# server for potentially stale date, you can set a time-to-live (in
# seconds) here.
local-ttl=300

# This allows it to continue functioning without being blocked by syslog, and allows syslog to use dnsmasq for DNS queries without risking deadlock
log-async

I used the fix from the reddit-Post, now it works. My current OS on the Orange Pi is Ubuntu Trusty Tahr.

[PromoFaux]

Ah, yeah apologies I meant /etc/dnsmasq.d/01-pihole.conf :)

OK, so it looks like Ubuntu in general starts networkmanager after dnsmasq

Thanks for the report!