Research indicates that the leadership of a school principal is a determining factor in school effectiveness, second only to the role of a student's classroom teacher. Yet, the species of "principal" is dwindling. National reports indicate that a great number of schools and districts are experiencing a shortage of a qualified pool of principal candidates. The dearth of principals is particularly endemic in districts perceived to have challenging working conditions, large populations of impoverished or minority students, low per pupil expenditures, and urban settings. In addition, conservative estimates suggest that roughly 40% of principals will retire this decade and that the number of principal positions needing to be filled will grow 20% in the next five years. But the principal shortage is more than an issue of balancing recruitment and retirement; retaining highly qualified principals has become equally problematic. The "revolving door" of the principalship has been fueled by pressure and demands that make the job nearly untenable. This study determines the nature and characteristics of the principal shortage (both current and impending) in Massachusetts. Responses to a web-based survey of Massachusetts' principals and existing licensure supply and demand ratios were collected and analyzed. Information gleaned from the data analysis was used to assist the Massachusetts Department of Education in determining how it can best recruit and support principals in the Commonwealth and better address issues of educational quality in this era of accountability.