Linux AND Windows VS HTB Machine


I was using mostly Linux so far vs boxes. But I am wondering can I use both Linux and Windows?

By that I mean… I connect to HTB via OpenVPN in Linux but then the Windows machine cannot access it.

So in a nutshell, is it somehow possible to use both Operating systems against the machine via “same” OpenVPN connection. (or can I connect to same box twice using Windows OpenVPN?).

I know I can do routing in VMWare but I hope that isn’t the only solution.

Thank you.