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Assume that my host is a Windows computer. I have Virtualbox installed and I put on it another Windows guest.

Assuming I connect with my host to a VPN provider called "A" with OpenVPN and with my guest I also connect to a different VPN provider called "B" and navigate on the internet through my guest on VPN B, would I effectively be "doubly " protected?

Can somebody explain to me how would this work exactly?

Would "VPN-inception" add 1 degree of protection every time one does it? (e.g, a virtual machine in a virtual machine in a virtual machine with each virtual machine having each a VPN connection to a different provider).

  • Please add more details explaining who is connecting where. The N in VPN stands for network, so somewhere there has to be a network, preferably with DHCP server, gateway, etc. Where is that place? – phk Oct 26 '15 at 16:19
  • I have tried rewording the question. All networking services are provided by the VPN client (OpenVPN). You just connect to your provider. – Con7e Oct 26 '15 at 16:29
  • How would that work if they're all coming off the same host which is the source? – Fiasco Labs Oct 26 '15 at 16:51

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