A few months ago I migrated almost all of my FreeNAS jails from Warden to iocage, but the OpenVPN one proved too much of a challenge.  I had another go today and now have a working OpenVPN iocage jail!

To be honest, not all that sure what I did differently in terms of the iocage configuration, as I followed this excellent guide both times.   I’m still running 11.1-U4 of FreeNAS, so no changes to the iocage networking that I thought was causing the original problem.

I actually got to the same point with everything configured and had the same problem, that the OpenVPN service just wasn’t starting.  Given my experience previously with OpenVPN in a Warden jail, I thought I’d try a full system reboot, making sure to stop the old jail from auto-starting and potentially conflicting with the TUN network configuration.

I can only assume that’s what was causing the problem, as when everything restarted and I checked the jail OpenVPN the service was up and running!

I copied across the client config to my MacBook and it connected on the first attempt.  I had to change a few of the Tunnelblick settings to get everything working perfectly, but testing inside my network appeared to be fine.

The acid test is how things work outside though!  I could only test this by tethering to my iPhone 4G service and all looks look.  The main test will be when I’m next away from home and need to connect back though…

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