It is to my understanding that Tor provides anonymity, meaning that people can see what you do, but don't know who you are, while with an encrypted VPN, you get confidentiality, meaning that people can't see what you do, but can get a general idea of who you are using your IP.
Would it be possible to obtain anonymity and confidentiality by using Tor and an encrypted VPN together? What would the best configuration for this? (on Linux, preferably)
Best Answer +LogicalApex , 02 June 2014 - 17:15
Wouldn't make a whole lot of sense... The whole point of a VPN tunnel is to push your traffic through that tunnel and out to and specific end point. If you were to access the VPN through Tor you would negate the major benefit of Tor. As you'll be forcing your traffic through a singular endpoint... Tor works so well because the actual endpoint you're pushing out via changes frequently. This often isn't the case with most VPN services...
The only thing this can hope to protect your from is deducing your actual IP address as you're hoping to mask it to the VPN tunnel. I'm not sure the extra complexity will actually gain you any real security in this regard.
You're better off just using Tor in a proper manner (booted via a live OS like Tails) than you would be by trying to essentially nest VPN tunnels.Go to the full post