What an oppressive regime could be targeting in this threat model: In addition, since your traffic has now egressed from the encrypted tunnel, if you use an unencrypted protocol like HTTP (not HTTPS/SSL), the oppressive regime can snoop on the full content of your traffic. Not only will the egress IP address associated with Tor or the VPN service be visible, but the final destination IP address will also be visible. Your traffic is now more susceptible at this point to the snooping of an oppressive regime. During that final leg of its trip, the traffic will no longer be tunneled through the Tor or VPN connection. Once your traffic has passed through the Tor or VPN connection, it needs to egress to its final destination, like, perhaps. However, since your traffic to Tor or the VPN is encrypted, they theoretically (unless you have already been compromised in some other way) can only observe that you are connecting to Tor/VPN and not decrypt the actual encrypted traffic itself. If you are connecting to Tor or a VPN service from home, this means an oppressive regime can see your home IP address connecting to an IP address associated with Tor or the VPN.
Oppressive regimes quite commonly have the ability to view traffic as it travels across ISP (internet service provider) infrastructure. We’ll start with the first threat actor shown above. That’s where equipping you with information can give you the ability use the service effectively without having to trust us with your raw data streams. However, we understand you may be in a position where you can’t afford to completely trust anyone – even us. The first of these is obvious, but the latter is of course ironic. For more information about tor and VPN opsec, see our article next Wednesday. Opsec is a set of best practices for remaining private while using anonymity networks. This article assumes that the user is using good operational security that will not out themselves while on the network. TL DR – In most situations, you are going to want to use User > VPN > Tor Should a Tor connection be tunneled inside an already established VPN connection, or should a VPN connection be tunneled inside an already established Tor connection? Before you can answer these questions, however, you must first consider your threat model. A big question for those who consider internet privacy essential is how to best use Tor in combination with a VPN service provider like Private Internet Access.
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