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