Testing VPN over Tor

I’ve setup a VPN over Tor configuration. How can I test that I’m actually connected to VPN through Tor?

I suppose it can be somehow done with nyx under sys-whonix qube but I cannot figure out how to show the full path of my connection (including the VPN server’s IP and the IP of the destination resource) and not just the Tor circuit one.

Also, maybe it’s even possible to see a richer log of which qube the connection originates from.

If the VPN is over Tor, then that is your exit point. Going to any IP test website like ipleak.net on an AppVM attached to the correct netvm will give you the answer.

What you are describing is sometimes referred to as “proxy chaining”.

The only way to really know proxy chaining is being done right is to have explicit netfilter rules in place so that only desired traffic at the desired points can flow. You want to also be able to observe those points (such as a tun0 interface) for desired traffic and also observe general points (such as a eth0 interface) for undesired traffic. Some of the threads on socks5 on this forum might help.

At this time, there is no developed ui, nor even complete documentation (documentation you can really rely on) for this subject. The nftables equivalent of iptables -P OUTPUT DROP, -m owner --uid-owner, and --gid-owner are your friend.

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whatismyipaddress dot com

I would reverse your setup (VPN → Tor) unless you have specific reasons for doing it this way. I’ve heard bad things about putting Tor in the middle. I forget the details but it’s something about an attacker being able to de-anonymize you by correlating web browsing patterns between you and the VPN