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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?

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  • That depends on the configuration of your VM. If you use NAT on your Network adapter it will do the trick. – CD Rohling Jan 12 at 11:59
  • Although you are taking a cybersecurity course, and you are using Kali, this is actually a pure networking question and not a security question. – schroeder Jan 14 at 12:33
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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.

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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.

  • OpenVPN is being set up on the Windows host, not the Kali guest. – schroeder Jan 14 at 12:32

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