Double VPN setup using VirtualBox

Hi guys

I've been reading a bit on this forum over the past week and couldn't find a definitive guide to setting up a double VPN connection so just want to check I have this right.

Host running Windows 7 with OpenVPN (+ dnsfixsetup.exe) installed and connected to a VPN. VirtualBoxgGuest in NAT mode running Ubuntu with OpenVPN.

So with the setup above and the VM guest in NAT mode would my connection go though the following?

browser -> VPN 2 (VM in NAT mode) -> VPN 1 (host) -> Internet

Any suggestions to improve this would be much appreciated

 

Why do you need this? If the VPN is configured right it should not leak dns.

 

Yes, that should be fine. But I don't use Windows hosts, and don't know dnsfixsetup.exe etc.

Because the VM is NATed to host, leaks are possible if the host VPN connection goes down. As I recall, you're safe as long as the VPN client is still running (even if it's not connected). I gather that dnsfixsetup.exe fixes that leak.

It's best to test using Wireshark on the host, looking at what goes out on the physical interface and on the VPN tap interface, under various conditions.

 

Thanks guys

dnsfixsetup.exe is from www.dnsleaktest.com/how-to-fix-a-dns-leak.php - I saw it mentioned on this forum.

I installed it because when testing my single VPN connection on the host OS (Windows 7), I tried a couple DNS leak test sites and my original location/IP was leaked. After installing the above, that is now fixed as it flushes every time OpenVPN connects.