Discovery System Functionality is Sorely Lacking

I have finished my Apple Watch evaluation periods, and there is no outstanding amount left on my watch, yet Discovery can't "cancel" the benefit so I can upgrade to the next Watch.

Discovery claims that had I ended the benefit earlier with an outstanding amount still to pay, an earlier upgrade would have been possible, but since I don't have an outstanding amount on my account I have to wait an additional 2 weeks.

How can this be possible? Who builds these systems?