Moonlighting by medical residents is a highly controversial topic that has recently received new interest and concern as states are implementing legislative and regulatory efforts to limit residents' work hours and as teaching hospitals are increasingly concerned about liability exposure. Despite the potential problems, moonlighting, or outside employment, represents additional income to residents that enables repayment of massive student loans and/or improves their standard of living. It means additional clinical experience and responsibility, which many feel enhances their educational experience, and it permits essential night and weekend coverage for community hospital emergency departments and walk-in centers. Because of these important considerations for residents, community hospitals, and risk management, the University of Massachusetts Medical Center has developed a unique approach to the problems of moonlighting that addresses the concerns of all involved parties. The development of extended employment guidelines has also enabled the medical center to maintain a detailed database on the volume of such activity.