We figured this out. It was an issue with the cellular carrier and not an issue in the Apple SDK. Things are working as expected now. Thanks for taking a look.

Also, I noticed when out in the field debugging that when the NWPath reports that it isUltraConstrained the path is always .unsatisfied. Is this expected?

Network framework supports WebSocket but not HTTP. Does this mean that there is currently no way to make an HTTP request with an ultra constrained path? Does it also mean a websocket is the only way to move data over an ultra constrained path?