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Ive been reading whonix's documentation and threads here to be more anonymous and secure.

For the best anonymity whonix recommends having two different computers, one being the gateway and the other being the workstation. On the workstation, for the best anonymity and security, would it be wise to run Tails as a live CD or USB, along with the whonix setup? I was unsure whether I should run Tails in a vm under whonix workstation, run Tails as a live CD and the whonix workstation as a vm, or just run Tails/the whonix workstation. I assume that would provide the benefits of both operating systems? Im not sure. (I've also had thoughts about running QubesOS and/or corridor as well, but then I had the thought that multiple types of OS's might increase my attack area). I have my gateway planned and almost setup but I do not have my workstation setup.

(also as a side note, when referring to Tor -> Tails over Tails -> Tor for security, does that mean run Tails as a live CD and use Tor browser or use vidalia and Tails in a vm? Im guessing the former. I know Tails > Tor is Tor in Tails, however I couldnt come up with any way to do Tor > Tails without using my setup at the beginning of the post)

Which configuration, that I have mentioned or your own idea, provides the most anonymity?

Trying to be my most paranoid self for safety :)

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One of Tails' main features is its amnesic feature. You forfeit that by running Tails in a VM.

Running Tails behind a Whonix-Gateway is recommended against, because it will result in Tor over Tor. See also:
Is running Tor over Tor dangerous?

No one has combined both projects yet due to considerable development effort, so at the moment there is no way to combine the advantages of both projects.

Full disclosure:
I am a maintainer of Whonix.

  • Is it possible to disable tor inside of tails? And on that note, if it is possible, would it then be wise to run a whonix workstation inside a vm inside of tails? Without allowing a tor over tor, of course. – user47946 Jun 7 '14 at 17:10
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    Is it possible to disable tor inside of tails? In theory it is possible to implement such a feature. But it has not been implemented. I posted a wishlist request, but wishlist means, it won't happen unless someone contributes the code and no one is working on it or promised working on it, so chances are very little. – adrelanos Jun 8 '14 at 8:02

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