Our scheduling system is supposed to catch this with a 28.5 hour buffer.
This happened as the result of a computer trade. If it is illegal or goes over a 28.5 hour buffer it is not supposed to allow the trade. So by my contract this is legal. That said I want to get home on the 25th. So since I am going to places like MKE and BOS in the winter the odd over me going over are pretty high.