App won't prompt to allow while connected to VPN

I have an app that connects to a device across a VPN. Glasswire won’t prompt to allow/deny while connected to VPN. If I turn the firewall off, it will work. Tried uninstalling and and performing a clean install and resetting windows firewall to defaults with no success. Any suggestions?

Edit: switching to “Click to block” works as well.

GlassWire typically cannot inspect individual app activity which uses a VPN, so won’t generate a prompt. But it sounds like there is some process which is being blocked. Perhaps a helper app which sits between the main app and the VPN. That at look at Active but Blocked apps and try to locate any likely candidate.