Skip to main content

FreeNAS: Using Transmission over OpenVPN (jailed)

FreeNAS sucks. but that's just my opinion. I set up FreeNAS to be a fileserver for all things on my local network so thought to utilize it as best I can for what's its capable of.


I want to have transmission on my FreeNAS server to work over OpenVPN. Transmission is installed via plugin which puts in into one of these FreeBSD jails.

trying to start openvpn up:

/usr/local/etc/rc.d/openvpn start


ug  6 23:19:50 transmission_1 openvpn[94497]: /sbin/route add -net  6 23:19:50 transmission_1 openvpn[94497]: /sbin/ifconfig tun0 inet6 fdda:d0d0:cafe:1300::100e/64Aug  6 23:19:50 transmission_1 openvpn[94497]: /etc/openvpn/update-resolv-conf tun0 1500 1553 initAug  6 23:19:50 transmission_1 openvpn[94497]: WARNING: Failed running command (--up/--down): external program exited with error status: 2Aug  6 23:19:50 transmission_1 openvpn[94497]: Exiting due to fatal error

things checked:

  1. all configs were in the right place /etc/rc.conf has openvpn_configfile="/usr/local/etc/openvpn/mullvad/mullvad_linux.conf"
  2. permissions on cert files: ca.crt, vpn.key etc
  3. permissions on scripts: /etc/openvpn/update-resolv-conf

checked all these, and no cigar.

now, I figured I need to manually execute the VPN setup to figure out exactly where this was all going wrong:

openvpn --config /usr/local/etc/openvpn/mullvad/mullvad_linux.conf

and now I can see this:

Sun Aug  6 23:56:51 2017 /etc/openvpn/update-resolv-conf tun0 1500 1553 init+ [ -x /sbin/resolvconf ]+ + [ up ]+ + [ tun0 ]+ + NMSRVRS=''+ + SRCHS=''+ /etc/openvpn/update-resolv-conf: ${!f...}: Bad substitution+ Sun Aug  6 23:56:51 2017 WARNING: Failed running command (--up/--down): external program exited with error status: 2+ Sun Aug  6 23:56:51 2017 Exiting due to fatal error

for some reason its not happy with the substitution around this array. Checking the code looked fine, and I couldn't figure out why it was unhappy at this point in the script.

Now some forums kept talking about having the shebang (#!/bin/bash) at the top of the config file (this made little/no difference and pretty sure that's not how the vpn config files work), for some reason I figured "#!/bin/sh" would be just as good = this was WRONG. The way 'sh' handles array substitution is different to 'bash' and so my error was in how my chosen shell was dealing with things. also,


find where your bash lives in jail:

[email protected]:~ # jls   JID  IP Address      Hostname                      Path     2                  transmission_1                /mnt/DARKNAS/jails/transmission_1[email protected]:~ # jexec 2 tcsh[email protected]_1:/ # which bash/usr/local/bin/bash

and put it in your /etc/openvpn/update-resolv-conf like so:

#!/usr/local/bin/bash# set -x## Parses DHCP options from openvpn to update resolv.conf# To use set as 'up' and 'down' script in your openvpn *.conf:# up /etc/openvpn/update-resolv-conf# down /etc/openvpn/update-resolv-conf

and your VPN should come up without a problem.

Local Networks & OpenVPN#

local networks on the same subnet will be accessible, but I learned you need to add other subnets to the routing table when openvpn comes up as I wasn't able to web into the transmission web GUI without the following:


172.16.40.x network is where my FreeNAS/Tranmission box lives

route add -net

/etc/resolv.conf issue#

my /etc/resolv.conf was not being restored after stopping VPN


this is a hack and possibly not a good long term solution

in /etc/openvpn/update-resolv-conf script, the 'up' part of my openvpn config file (i.e. /usr/local/etc/openvpn/mullvad/mullvad_linux.conf) worked fine, but the 'down' process basically did this on the tun0 interface and walked away:

/sbin/resolvconf -d "${dev}.openvpn"

after not being able to find a solution i came across a forum where dude just added copy and mv commands to backup then restore the default resolv.conf file

# in the up 'case'cp /etc/resolv.conf /etc/resolv.conf.default
# in the down 'case'mv -f /etc/resolv.conf.default /etc/resolv.conf