Never tested it, but I can image it might be better to use offline transfer of the licenses.

I have utilized PCS7 development licenses that are hosted on license servers through a VPN tunnel. This works fine (at least through the corp. tunnel/client I use [AT&T Global Network Client V7.3.0.3002].

I have not tried to manage the license servers through VPN but see no reason it shouldn’t work.

I do recommend that you copy the license local on your license server (or system with ALM is running) and then Remote Desktop to the system and upgrade /install the licenses. I copy them to a drive with no licenses on it for upgrading license and then point the update at that drive.