Virtualbox and OpenVPN connections

I taking training on web application hacking and the professor is asking me to ssh to attack machine and do hacking.

I am using Kali Linux at home and using Virtualbox. The professor allows OpenVPN to connect. If I connect via OpenVPN to his platform with my Windows machine, shall I be able to use Kali? Will NAT take care VPN-related issues when I attack from Kali?

Once I ssh to attack machine, can I use kali over OpenVPN?

2 Answers

It all depends on your VirtualBox machine setup. NAT configuration in such an instance would relay all your traffic trough your OpenVPN configuration, while Bridged Adapter configuration would ignore your local OpenVPN setup if it’s not running in the router or switch software.

So if I connect via open VPN to his platform with my Windows machine, shall I able to use Kali? Does NAT will do take care VPN related issue when I attack from Kali?

Your virtualbox should forward connection irrespective NAT/bridged mode, from kali. Your virtual machine will use the same routing as the host OS windows. It should just work fine.