Programming Wing Issues with Mac

I have an EOS Programming Wing that I am trying to connect to my Mac Laptop.

The problem is that when connected, the keypad doesn't work nor do any of the encoders.

The Mac is a 2016 15" MacBook Pro running 10.15.3. I have connected the wing via a USC C dongle with USB A ports as well as a direct connector without the dongle and using a USB-C to USB-B and a USB B to C cable, no adapter. I've restarted each time, and still no luck.

The Mac recognizes the Nomad Key in the Wing, and it lights up as it should, but the keypad functions don't work. The External keyboard also doesn't function, when connected, but I disconnected it just to elicited potential conflicts.

The wing and attached keyboard and trackball all function as expected when connected to a Nomad Puck.

Any thoughts or suggestions?