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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.

  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.

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.

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.

1
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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.