Directors of education in Greece operate at prefectural level and are the heads of the local directorates or bureaus of primary/secondary education. Because of the centralized character of the educational system, their role is restricted to facilitating the smooth operation of the local school system and implementing the national policy on school education. The research reported in this article aims at investigating the job stress experienced by the Greek directors of education. Three hundred and fifty-seven Directors of Education took part in the study. The two main questions addressed concern: (1) the level of job stress experienced by the participants; and (2) the main sources of their job stress. The results showed that directors of education in Greece experience moderate occupational stress while the main sources of their work stress come from different domains including the shortage of human and financial resources, the implementation of national educational policies and reforms, the nature and the characteristics of their work, their relations with people and specific dimensions of their career. Moreover, variations were found between the different subgroups examined with directors of secondary education and directors of directorates of education reporting higher stress. (Contains 3 tables.)