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This chapter examines the moral dilemmas mentors from three different groups (Jewish, Druze, and Arab) encountered in Israeli Arab schools, how they manage these dilemmas, and how the nature of particular dilemmas might connect to their management strategies. Given the multicultural and politically conflictive context of Israeli society, a cultural and political reading of in-service mentors' moral dilemmas reveals that mentors' encounter and management of recurrent moral dilemmas is embedded in cultural and political issues that seem to hinder their mentoring practice. Preparation programs need to highlight awareness of mentors' own culture and that of their mentees in order to implement a culturally and politically responsive practice.