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I have install a VPN on my computer and connecting TOR throught it. How can I check that the connection really goes throught VPN ? I can't just goto any "what's my IP" page as this will just return the exit node IP I want to know what IP the entry node sees

any ideas ?

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I don't know if this will work but try the traceroute utility and if it shows the VPN server you are connected to, that means you are connected or maybe try pinging the IP of the server you are connected to?

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Well, first of all - you need to use Linux or FreeBSD box or VM for that. At that box you're connecting through VPN and after that it depends on what your VPN is giving you in a matter of the IP:

  • NAT - worst scenario, because it usually also grants you a dynamic and sometimes also a private IP. In this case you need to route tor process' user - it's a deian-tor or tor usually - through the firewall by user basis to use the tunX device of your VPN making an exception for all private networks. And - if your VPN ip is a private one - make an exception for this network in your firewall rules
  • Direct IP - even if it's a dynamic one, there's no problem, just route tor's user through the device and make all the private networks an exception.

Only after that moves your entry guard will see the VPN server as a query originator for sure. Do not use Windows for that tricks - even using a ProtonVPN-like apps that do offer a per-application routing settings, leaks happening

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