Thursday, May 7, 2020

Use a VirtualBox Windows 10 guest as a jump host to a remote VPN

In some occasions you want to keep your host machine clean from dodgy VPN software. A solution is to use a virtual image as a jump-host (or stepping-stone). In the following steps you will learn how to use VirtualBox and a Windows 10 guest.

  • Setup a Windows 10 guest OS in your VirtualBox machine.
  • In VirtualBox image settings, set network to "Bridged Adapter".
  • Start a VPN connection on the guest image.
  • Get the IP address.
  • Create port-forwarding rules on the Windows 10 machine:
    netsh interface portproxy add v4tov4 listenaddress=<IP address of the virtual machine, starts with 192.> listenport=<port vm> connectaddress=<IP adress of the target> connectport=<port of target>
  • In the previous step, the target is a webapp. On your host machine, go to your internetbrowser and browse to 192....:<port of target>.

To list which port-forwardings are active on the Windows 10 guest, run command:
netsh interface portproxy show all

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