Using Virtual Private Networks (VPN) and Tor Together
The issue once you get to need such a level of security that you find yourself categorized in a paper like this is you are really the only person who knows what you need to keep yourself safe. That presents an issue in itself because you are hopefully reading this paper to gain some knowledge. I however, am not the type of individual to be able to relate very well with you but I can tell you a philosophy a friend told me a few years back that has stuck with me since. “When you are literally fighting for your life online, NEVER put all your trust into one company or service”.
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To attain maximum security, privacy, and anonymity, one needs to be sure they aren’t putting all their cards down in one area and not focusing on others. An example of this would be just using the Tor network to attain Internet anonymity. This is an “okay” model to follow if we assume the Tor network is as secure as it is made out to be. However, recent events have unfolded that claim otherwise (http://gizmodo.com/judge-confirms-carnegie-mellon-hacked-tor-and-provided-1761191933). Instead, you could purchase 2 very reputable VPN providers like say IVPN and CryptoStorm, and then chain them together in succession before using the Tor Browser Bundle. You would need to be cautious that no IP leaks were happening in the process but say if you connected to the first VPN on your host OS and then ran Debian from a VirtualMachine, you would be able to connect to another VPN provider within the Virtual Machine and attain a very high level of anonymity and security. Not only would this really limit your attack vector, but it would be like making your own little Qubes by compartmentalizing that section and keeping it separate from the rest of your system.
IVPN provided a really great tutorial on using Virtual Machines, VPNs, and Tor together to acquire pretty complete network anonymity. I would highly recommend their “Privacy Guides” section of their website here: https://www.ivpn.net/privacy-guides/ These guides are very well written and provide a second perspective from my own.