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If one decide to cover the usage of Tor from both front end and back end (meaning both from ISP and the destination page) using VPN and/or Proxy, What process should one go through? For example the following scenario:

User ---> VPN1 ---> Tor ---> VPN2 ---> Destination address

or

User ---> proxy1 ---> Tor ---> Proxy2 ---> Destination address

This is in a case when Tor is used via Tails.

For the purpose of this question Both VPN1, VPN2, Proxy1, and Proxy2 are assumed to be free of charge. Therefore, there is no money trail.

What is the details of the setup required to be able to do this?

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  • I don't exactly understand what is ment by this. Isn't Tails an operating system used to contact Tor without making a dent in the computer? I don't understand the user connecting to tails?
    – Aurora
    Dec 23, 2014 at 18:31
  • @Aurora Dear Aurora, I edited the question to make it clear. What I mean is to use a VPN before connecting to entry guard and to use a VPN after the exit node of Tor while using Tor via Tails.
    – Roya
    Dec 23, 2014 at 18:50

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This is pretty complicated to do, but it is possible. Assuming that the VPN you are connected to only uses TCP then this could work, though not easily.

You could do this with much less complication using a few socks5 proxies. You could use a standard proxy to contact a bridge. Then, you would have to send a new packets to your other proxy.

The problem with this is the fact that it isn't the most convinient thing in the world. Granted, Tor isn't convinient either, this would not be fun to do, as it would require some study of the VPN your are connecting and/or the socks5 protocol (assuming you use socks5).

A much easier way to preform this kind of task is to connect to your vpn, then to the Tor network, and finaly to your proxy (this would cut down on time considerably, as there are simple tools to "torrify" ports though I have not personaly used them)

In stort, you can do it, but it will not be fun.

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