How To Use OpenVpn With DnsMasq

And of course we want these rules activated every time Ubuntu boots up, so we add them inside /etc/rc.local:

#!/bin/sh -e
# rc.local
# This script is executed at the end of each multiuser runlevel.
# Make sure that the script will "exit 0" on success or any other
# value on error.
# In order to enable or disable this script just change the execution
# bits.
# By default this script does nothing.
iptables -A FORWARD -m state --state RELATED,ESTABLISHED -j ACCEPT
iptables -A FORWARD -s -j ACCEPT
iptables -A FORWARD -j REJECT
iptables -t nat -A POSTROUTING -s -o eth0 -j MASQUERADE
service dnsmasq restart
exit 0

Please notice the line before the last one:

service dnsmasq restart
This is crucial: During system startup dnsmasq tries to come up before OpenVPN does. But without OpenVPN there is no tunnel interface (tun0) present so naturally dnsmasq fails. A bit later, when /etc/rc.local is read the tun0 interface is present, so at this point we restart dnsmasq and everything is as it’s supposed to be.
And this how you can use openvpn with squid and pihole (Pi-hole is using dnsmasq and after the system was restarted pi-hole and openvpn weren’t working anymore).

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