In the CUPC client, I noticed that under Help > Show Server Health the VVM System status is showing as "Disconnected" when using port 443. Switched it to port 80 just to test and the status changed to "Connected". As per the deployment guide and personal preference, we definitively prefer port 443. Interestingly, functionality does not seem impaired when using port 443 with the Disconnected status, but am curious why this is happening.
Opened a TAC case as well and tested a few things like whether port 443 was listening on the Unity Connection box and so on and everything checked out.