virtualbox.org

I can't seem to figure it out.

Despite running NordVPN on OS X before the VB startup, VB is still leaking my IP, which is a huge security risk.

I can run NordVPN within VB, but that doesn't quite give me peace of mind.

Ideally, I'd like VB to register the initial redirect from NordVPN, and then run a second instance of NordVPN within VB to provide a second redirect.

Can it be done?

I have no idea. Why don't you ask them? They claim that you can use two devices.