This research study was designed to build grounded theory about the challenges faced by rural superintendents. Participating rural superintendents identified five areas that presented a challenge but that also applied to superintendents in other settings: school law, finance, personnel, government mandates, and district or board policies. Further, these superintendents identified challenges related specifically to the rural setting and to their lack of acculturation to the demands of rural school leadership. Focus group research conducted among rural superintendents in New York, Pennsylvania, and Tennessee indicated that the challenges of the rural superintendency were distinct enough to warrant some specialized preparation for such service. (Contains 1 table.)