In recent years several companies have offered employees the opportunity to transfer out-of-the-money options to a financial institution. This paper is a clinical study of a high-profile program offered by Microsoft in 2003. This program contained some complexities that likely made it unattractive and contributed to a low rate of participation. The counterparty, JPMorgan Chase, though profiting up front, failed to hedge an element of the risk it accepted from the employees and lost nearly the entire value it paid for the options. The experience has important implications for the design of programs that offer liquidity to employee stock options.