Quote from: MrJoshua on September 03, 2013, 01:55 amQuote from: Nightcrawler on September 03, 2013, 01:05 amYou do realize that Tails is based on Linux, do you not? As a general rule, you cannot run Windows software on Linux (at least not without jumping through any number of hoops.)Yeah, I was just using that as an analogy.Lots of posts are talking about using VPNs now and TAILS seems to be a favored operating system, so my question is, how do you install and run a VPN software program with TAILS operating system? In Windows you just open the OS and download the VPN software and run that, but how is it done with TAILS.Like I said it's not recommended. Here it is straight out of the horse's mouth: Q: Is it possible to use Tails OS to connect to a VPN instead of Tor? There are times I need faster speeds. I understand it will lose some security.A: It's a very fundamental assumption of Tails to force all outgoing traffic to anonymity networks such as Tor. I don't think we want to provide ways of going around this since it would possibly compromise the security of all Tails users.If you want to use OpenVPN with a live distro and without Tor I bet you can use any Debian or Ubuntu derivative and install OpenVPN from it.Comment by Tails  Fri 01 Jul 2011 11:17:36 AM CEST Source: https://tails.boum.org/forum/Possible_to_connect_to_VPN_instead_of_Tor__63__/Also see the discussions at: https://tails.boum.org/forum/Tor_with_VPN/#comment-ccfa0e5cd004824bda5e9096f92a1c26Tor with VPNQ: If I connect to a VPN via the host machine and run a Tails VM are there problems with this scenario? From my understanding the TOR entry and exit nodes will see the VPN IP?  Also are the message contents still encrypted by TOR once they enter the VPN? That is while the VPN sees the IP of the TOR exit node, the contents are still TOR encrypted in the last   hop to the TOR VM.  If I connect to a VPN via the host machine and run a Tails VM are there problems with this scenario?A: Not really, but this depends on what you mean with "problems". Your VPN provider will learn your Tor entries (and hence your entry guards) and in general have the same power as your   ISP normally has over you. Hence make sure you trust your VPN provider at least as much as your ISP.  From my understanding the TOR entry and exit nodes will see the VPN IP?A: That is incorrect:  The VPN provider will know the IP addresses of your computer and your Tor entry node.  The Tor entry node will know the IP addresses of your VPN provider and your middle node.  The Tor middle node will know the IP addresses of your Tor entry and exit node.  The Tor exit node will know the IP addresses of your middle node and final destination.Hence no one but you know the entry and exit.Adding a VPN into the mix changes nothing from Tor's side; if the exit would be able to see your VPN provider's IP address it would be able to see you IP address when not using Tor, so there would be no anonymity. Luckily this is not the case.Q:  Also are the message contents still encrypted by TOR once they enter the VPN?Yes. The VPN encryption is removed at the VPN provider, and the last (third) layer of Tor's encryption is removed at the Tor exit.  That is while the VPN sees the IP of the TOR exit node, the contents are still TOR encrypted in the last hop to the TOR VM.Your VPN provider will know nothing about your Tor exit.Comment by Tails  Thu 01 Mar 2012 10:45:42 AM CETComments on this page are closed.Last edited Mon 15 Apr 2013 09:45:57 PM CESTHope this answers your question. Nightcrawler4096R/BBF7433B 2012-09-22 Nightcrawler <Nightcrawler@SR>PGP Key: http://qtt2yl5jocgrk7nu.onion/pks/lookup?op=get&search=0xB8F1D88EBBF7433B (IndyMedia .onion keyserver)PGP Key: http://dkn255hz262ypmii.onion/index.php?topic=174.msg633090#msg633090  (Silk Road Forums PGP Key Link)PGP Key Fingerprint = 83F8 CAF8 7B73 C3C7 8D07 B66B AFC8 CE71 D9AF D2F0