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At times, I would like to run Tails/Tor through a VPN. If I am able to install a VPN software into Tails, does anyone know how I would be able to keep the newly added software in Tails; perhaps by creating a new ISO off the modified Tails OS? If so, how would I do this?

Thanks, Doe Joe

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I'll assume that "Tails/Tor" is just "Tails". Running Tor without tails on your laptop OS (windows or whatever) is trivial as is setting up a VPN in front of it. So assuming your only talking about Tails...

I would like to run Tails/Tor through a VPN

What you want is currently a feature request (#5858) but has not been completed yet. It's a 5 year old request, so no grantee that it will show up in the next release.

In the feature request is a script to install and run openvpn inside tails. The script runs the VPN over Tor, instead of what you asked which is to run Tor over the VPN. It's a rather complex script and isn't really plug-and-play.

To get the VPN in front of Tor, like you asked, you'll have to wait for the feature request to get completed, or run the VPN though your home router or other device.

A simpler option would be to install the VPN software on your laptop then run tails inside a VM (on your laptop) while connected to the VPN. Here's the official documentation (and warnings) for running tails inside a VM

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