[OPSEC/Computer] Tails/TOR/VPN/Whonix? Please help

Is there a way to run a VPN with tails? I ask because they way I understand it using tails and TOR will still let your ISP see that you are using TOR where as simply using a VPN and then TOR will hide the fact but leave you with a static workstation should anyone launce a browser based attack.

I thought about whonix but it isn't amnesiac is it?

My goal is to have an amnesiac VM (phrasing?) that will run over a vpn that I can then run TOR through. I want to hide the fact that I'm using TOR from my isp, be able to use TOR, and then not have to worry about having my system permanently infected if someone injected some sort of attack while I was visiting a website like what happened with SR and freedomhosting.

Is having that combo of 3 doable and if so can you help point me in the right direction?

I could just run tails/tor but I don't like my mr internet man knowing I'm using tails or TOR.


Comments


[1 Points] kamn74:

Unfortunately, Tails isn't set up with the software to connect to a VPN.

https://tails.boum.org/blueprint/vpn_support/


You can use a Tor bridge with Tails. An unlisted bridge should help prevent your ISP from knowing that you are connecting to the Tor network:

https://tails.boum.org/doc/first_steps/startup_options/bridge_mode/index.en.html

https://www.torproject.org/docs/bridges


You can use a SOCKS proxy to connect to the Tor network.

https://tails.boum.org/doc/first_steps/startup_options/network_configuration/index.en.html

This company offers a SOCKS proxy. Other VPN services probably do as well:

https://www.privateinternetaccess.com/pages/client-support/ (Use Ctrl-F to search for SOCKS)


You can run Tails in a virtual machine using VirtualBox and have your host system running a VPN. All network connections from Tails will then be routed over the VPN.


You can purchase a router pre-flashed with software to connect to a VPN and connect your Tails machine behind the router:

http://www.flashrouters.com/


[1 Points] not_secure_at_all:

So if I'm running windows I can run my VPN as usual and run a VM, and boot tails into the VM? Am I understanding this correctly?

Also I thought there were some VM's that kinda reset themselves after every session and that's why they were good for testing viruses and such.


[1 Points] not_secure_at_all:

I understand windows has issues but I don't have much of a choice. Given this what software would you run? I think if I'm at the point to where someone is backdooring me then it doesn't really matter what I do