On 01/21/12 at 03:44 PM, Christopher J. Walters wrote:

 > 2. What is the best way to use a VPN with Tor to increase anonymity?

 You're not going to get better anonymity by using VPNs with Tor. Anonymity is 
what Tor does very well, far better than any commercial VPN arrangement. With 
VPNs, there are potentially always logs that lead back to you. You can make the 
trails hard to follow, by nesting VPNs from multiple providers and paying 
anonymously, but you can't eliminate them.

 You can use VPNs with Tor in two ways. You can route Tor through VPN services. 
That prevents your ISP etc from seeing that you're using Tor. Generally, VPNs 
are more popular than Tor, so you won't stand out as much. Once the VPN client 
has connected, the VPN tunnel will be the machine's default Internet 
connection, and the Tor Browser Bundle will route through it.

 You can also route VPN services through Tor. That hides and secures your 
Internet activity from Tor exit nodes. Although you are exposed to VPN exit 
nodes, you at least get to choose them. If you're using VPNs in this way, 
you'll want to pay for them anonymously (cash in the mail, Liberty Reserve, 
well-laundered Bitcoin, etc). However, you can't readily do this without using 
virtual machines. And you'll need to use TCP mode for the VPNs (to route 
through Tor). In our experience, establishing VPN connections through Tor is 
chancy, and requires much tweaking.
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