Much recent research on educational organizations, including that of Meyer and Rowan (1977, 1978), has depicted them as ritualistically legitimated, internally loosely-coupled systems. Willower, however, has argued (1982) that legitimization of schools by their communities is not merely ritualistic but is ordinarily problematic. To examine principals' perceptions of the problems posed to their schools' legitimacy by teacher misconduct and the manner in which they learned about and reacted to such misconduct, half-hour to one-hour interviews were conducted in January and February 1983 with 45 senior high school and junior-senior high school principals in a diverse 7-county area of a large northeastern state. The bulk of the incidents principals recalled dealing with teacher misconduct concerned student-related "damaging" teacher behavior. Principals tended to be sensitive to the potential impact of teacher behavior on a school's image and were quick to give attention to any problems that might threaten the legitimacy of their organizations. Findings of the study do not confirm Meyer and Rowan's and other recent accounts emphasizing ritual legitimization; rather, they suggest how problematic legitimization ordinarily is for schools and how tightly bound administrators and teachers are to each other in containing potential threats to school legitimacy. (JBM)