Let your plans be dark and impenetrable as night, and when you move, fall like a thunderbolt.

Using a VPN With Tor

The question comes up semi-regularly: “Should I use a VPN to connect to Tor?” and “Should I use Tor to connect to a VPN?” and various combinations of Should I use Tor to VPN into a VPN to connect to Tor via VPN… with Tor.

The developers at the Tor Project (whom I respect immensely and believe know what they’re talking about) have a unilateral policy for this to never use a VPN to connect to Tor. Here’s a snippet from a recent discussion on the tor-talk mailing list:

...if somebody somehow breaks the anonymity of your Tor
circuit, it's nice to have another layer behind that. But if somebody guesses that you're using a particular VPN, or you pick a VPN that they're already monitoring for other reasons, then you basically let them see the beginning of your circuit when otherwise they might not have been able to.

In this he’s saying if you’re using a VPN to connect to Tor, you’re putting yourself at greater risk because the VPN service has a log of your information, your connection times, and the fact that you made a connection to Tor. This is supposed to be higher risk because if a nation state decided to perform passive monitoring, the place they would start is the VPNs. (He also compares this to having a consistent first hop guard node that everyone uses but I’ll leave that debate for another day.)

He’s Right… Sometimes

Dingledine’s logic is sound and if one were to have a policy to share with a community, it should be this one because it puts the least amount of risk on tor users. But, as with most things related to security, a unilateral policy is not always the best one. You need to know your threat model.

The Case of the Harvard Bomber

There is a now famous case of student at Harvard who had not finished studying for his finals and decided he wanted to email a bomb threat into the school to stop tests from happening. He went back to his dorm room, fired up Tor Browser, and sent an email from Guerrilla Mail to the school.

In this case, tor protected his anonymity. The email could not be traced back through the Tor network and to his IP address. Tor did it’s job. His downfall was that he made the connect to Tor from his dorm room. The university admins simply went back and found all the tor connections at the time of the email, and found that it was a very small segment of students. The police went to each of those students and eventually found their man.

What if the Harvard Bomber used a VPN to first connect into Tor? Would it have saved him? Maybe, or at least it would have made it more difficult. He would connect into the VPN service used by hundreds or thousands of other people, and then connect into the Tor Network. This might mean that even when they noticed the Tor traffic, they wouldn’t be able to attribute it to a specific student because there would be no log of them connecting to the Tor network. (That being said, Harvard could subpoena the VPN provider and try to determine which of the VPN users were from Harvard and which of them connected through Tor but I’m trying to make a point. :) )

When to VPN > Tor

Here’s when you might want to use a VPN to connect into Tor:

  • Geographic fingerprinting: You are from a small village with not very many Tor users. If there was a suggestion that sketchy activity has happened, they would knock on your door first. Especially if your operation was geographically specific (like a bomb threat).
  • Untrusted ISP: You know that your ISP is monitoring, logging, and sharing your connection information (hint: they are). You could make a choice to hide your connection details from your ISP and instead give that responsibility to your VPN service which you have more trust for.
  • Plausible Deniability: You could rely on the fact that thousands of other people are using the VPN service at that same time so it’s difficult to correlate activities to an individual.
  • Jurisdiction Diversity: It’s easy for most organizations to issue a subpoena to a company in their same company. It’s also easy for any of the 5, 9, or 14 Eyes to target services in their shared jurisdictions. If you have a VPN provider that is not in one of these jurisdictions, you can use them to make it harder to issue subpoenas to.

When to Tor > VPN

This is a bit more difficult to accomplish but possible. The issues here are you have to make sure you’ve purchased a VPN service anonymously, make sure that it allows connections via tor, and make sure it supports TCP as tor is a TCP-only protocol. The only scenario I can think of that you would need this is:

  • Tor Blocked: Less of a security issue and more about usability, if a service blocks all tor exit nodes, you can try to use tor to hide you connection into a VPN service which is unlikely blocked.

That being said, this is a really bad idea because when you have a consistent endpoint you connect to, it could have unknown consequences to your anonymity. This is the main reason that Tor switches circuits regularly instead of using the same circuit every time.

When to VPN > Tor > VPN or Tor > Tor

Now we’re getting nutty but we can think it through. You’ve made the choice to connect to tor via VPN, why not make another hop and just connect to another VPN service via Tor. Or, if you think 1x tor is pretty good, so 2x tor must be even better! Use cases:

  • You’re nutty: Generally if you think there is an undisclosed vulnerability in tor, that is actively being used, but you still think that tor is the best option, you want to protect yourself by layering methods on top of tor.

Whatever your rationality, know that this method has not been tested to see if it maintains your anonymity. There are so many edge cases of mis-configuration, fingerprinting attacks on the service, and plausible statistical attacks on your connection, you shouldn’t assume this makes any sense.

Further Reading

VPN’s are just one example of laying protections on top of tor. You could us private VPN hosted on a VPS, or SSH service, or if don’t understand any of this, a proxy. This debate comes up so regularly that lots of groups have posts and wiki pages about it. Check out the links below for additional information: