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I would like to know how I can tunnel a VPN thru TOR. Like so,

ME ---> TOR ---> VPN ---> WEBSITE

This way, my visible IP address is that of my VPN, and not the TOR exit node. And, my VPN's traffic is tunneled thru the TOR network and comes out the other end.

Is there any easy way of doing this on Windows 10?

Considering many websites block traffic from TOR exit relays, I'd be surprised if there wasn't an easy way of configuring this kind of setup.

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From: https://privacy.net/what-is-tor/

Tor over VPN:

With Tor over VPN, you connect to the VPN first, then use the Tor browser. It’s simple and effective.

Your traffic will go through the VPN server before it gets to the Tor entry node. This means that the VPN server can only see that you’re connected to Tor and can’t see where your traffic is going. Going back to your ISP, it only sees that you’re connected to a VPN server, and nothing beyond that. This means your ISP can’t see that you’re connected to a Tor entry node.

VPN over Tor:

This setup is a little more complex and doesn’t really offer additional anonymity. In this case, your traffic goes through Tor first. Your ISP can still see you’re connected to the Tor network, the Tor entry node can see your real IP address, and you still need to trust you VPN as it can see where your traffic is going.

One issue VPN over Tor does alleviate is the Tor exit node being able to see which site you’re visiting. Instead, it simply sees that you are connecting to a VPN server. One downside to this is that your VPN login information could be viewed by the Tor exit node operator. Another benefit of this setup is that websites which normally block Tor traffic will be unblocked.

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  • Oh, really? Maybe I'm not describing the problem correctly. So, there is no way to connect to a VPN after exiting a TOR exit node? I thought maybe that was doable. – watchy Sep 27 '20 at 19:34
  • Perhaps I misunderstood. Let me update my answer. – Aviv Lo Sep 27 '20 at 19:54
  • Yeah, the second option is what I am trying to do (on Windows 10). – watchy Sep 27 '20 at 20:18
  • Do you know how to setup a socks proxy? – Aviv Lo Sep 27 '20 at 20:42
  • Yes I can do that. At least, in regards to configuring TOR that way (using the torrc file). – watchy Sep 27 '20 at 21:10
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Simply include the option socks-proxy server [port] in your OpenVPN client configuration, and it will use Tor as a socks proxy.

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Here is a link how to do it: https://privatevpn.com/blog/guides/80/how-to-connect-to-privatevpn's-openvpn-servers-over-tor

It is what user 2020 said. You need to rout VPN traffic over (local) proxy tor. For this you got to edit the ovpn file. OVPN are configuration files for openvpn. It is an open-source vpn program. Nearly every VPN provider works with it and builds its own program based on openvpn.

So:

  1. you'll need to get openvpn and install it.
  2. Get the ovpn files with your VPN provider. You most likely will have to have a paid subscription.
  3. Find out the IP-address of your entry/guard node.
  4. Edit the ovpn file you'll want to use: at the end write:
socks-proxy 127.0.0.1 9050
route [IP of your entry guard/node] 255.255.255.255 net_gateway

tor has a build in proxy you can use it to connect to from other programs. 127.0.0.1 is the loopback address. That is essentially your own PC. 9050 is the standard proxy port of tor. Route changes the Routing table (for further explanation of the routing table, google that one. It is too much too explain here). Changing the routing table might not be needed in Windows other than in Linux. You could try it first without the last line.

  1. Use openvpn with the edited ovpn file to connect to VPN over Tor.
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Late answer, but this may help others who wish to achieve the same.

This takes a little circuitous route, but IMHO more safer than other options provided.

Download and install Whonix from here, then follow the steps mentioned here & an example setup here to achieve User > Tor > VPN > Internet

Why Whonix?

DNS leaks are impossible as all connections are forced through Tor or blocked.

Few things to consider:

  1. UDP-style VPN connections are incompatible with Tor; the VPN must be configured to use TCP.
  2. Using Windows 10 there are high chances of DNS leaks through your VPN. If you connect to a VPN network on a Windows machine for instance, smart multi-homed name resolution may lead to DNS leakage.

https://superuser.com/questions/1512544/vpn-dns-leak-when-using-openvpn-on-windows-10-december-2019-specifically-wit

https://www.ghacks.net/2017/08/14/turn-off-smart-multi-homed-name-resolution-in-windows/

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