OpenVPN (+killswitch) with Transmission guide for 9.10-STABLE?

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NigelNoFriends

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TL;DR: I am trying to find out if it's possible to rout all the incoming/outgoing traffic for a jail through a VPN service?

After having problems (probably user error, but I've read others are having similar plugin breaks on 9-10-STABLE) configuring multiple jail plugins (e.g. Sonarr, SabNZB, Tranmission etc.) to talk to one-another and the web, I have decided to try running an Ubuntu VirtualBox jail instead, and install all the full programs normally through the OS.

Presently, I have a bridged dedicated VPN router (OpenVPN via DD-WRT), but it's a clumsy setup and the router is a bit older so bottlenecks everything with a 10/100 network and 300Mb Wi-Fi connections.

So. I am hoping it might be possible to either direct the jail's traffic exclusively to use a vpn (and kill switch would be great!), or alternatively achieve the same result from within in the virtual box i.e. setting it up (somehow) though the virtual Ubuntu OS?
That way, I could connect the FreeNAS back up to my primary router and get rid of the subnetwork.

I'm still very new to FreeNAS and networking in general - so what I'm asking may not be technically possible - but I've not been able to find anything helpful on google to-date - at least not what I am trying to achieve (I've read a couple how-to's in the for a distinct OpenVPN jail or routing one particular program through - I thought I cam close with this forum how-to, but couldn't get it working. (For all I know that a round peg I'm trying to put into a square hole?)
 
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NigelNoFriends

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NigelNoFriends

Explorer
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Mar 29, 2016
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56
Did you find the answer to this?

not entirely - hoping someone with write a new (or update their old) how to...

Though, this one was good for installing (I think), but I can't find how to actually test is the vpn component is working. I am also hoping to implement a kill-switch, but unsure if following another guide will break the transmission/opnvpn install.
 
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