I’m at a loss here and was hoping someone with more networking knowledge can explain why I am having this issue. I use a private VPN on all of my devices. However, I find that I need to disable it in order for HTB to work reliably. While it works with HTB for most things, sometimes I am unable to SSH into a target box, etc.
My set up is Ubuntu host connected to mullvad VPN with a Kali VM guest (virtualbox) on top and connected to HTB VPN. I can confirm that the host VPN tunnel is active for all of the connections while on the guest Kali VM. I can usually enumerate the target boxes and interact with their services, but sometimes some of them don’t work and only start working when I disable the host VPN. Can anyone explain why? I can provide more details of my setup if needed, but I imagine there is an obvious reason here that I am just missing!