Recuring VPN problems


I have been using HTB for a few years. I tend to jump around on different computers. Most of the time I use my PopOS machine for the purpose of pentesting/hacking. But sometimes I use my Mac which Is my daily driver. Now and then I am located at my stationary machine at home which is a Windows 10.

I know Kali is the name of the game for most people but my way of doing this is spinning up Kali in containers for every new project (box) I start working on.

Through the years connecting with OpenVPN stopped working on just about every machine for some time and then suddenly started working again. Right now OpenVPN does not work with either MacOS or PopOS right our of the box. Right now I use Open VPN Connect 3.4.3 (4617) on Mac OS 13.5 (22G74) and I am unable to connect.

On PopOS It does not work using the GUI but I can make it connect from the CLI. I did not dig deeper into that issue but from time to time through the years it worked and suddenly it stops working.

I don’t know if Kali Linux is the only supported platform from HTB??? But It would be really really nice if the VPN connection could be independent of platform and always supporting the latest version of OpenVPN. I understand that sometimes there is a problem when OpenVPN releases a new version of the software but still I do not experience this amount of problems with any of the other VPN-connections I tend to use from my machines.

This recurring VPN-problems are what’s annoying me to the degree that I sometimes stay away from HTB. I imagine It can’t be that hard to make this work but I’m not a network guy…