How do I verify Tor through VPN?

Question

I have a VPN -> Tor setup. I'm running Tor in a virtual machine while connected to the VPN from my host.

Now, how do I verify that I in fact do enter Tor through the VPN?

Answer 1

Install Wireshark on the host machine and the VM. I see three places to capture:

1. the host physical NIC;
2. the VPN tun interface in the host; and
3. the virtual NIC in the VM.

Capture 1 should show encrypted VPN traffic with the login server. You should see no Tor traffic there, because it's encapsulated in the VPN packets. Captures 2 and 3 should show encrypted traffic with your entry guards. You should see no plaintext traffic there, because it's encapsulated in the Tor packets.