This paper examines the nature of moral dilemmas mentors from three different national groups (Jewish, Druze, and Arab) encounter in their work in Israeli Arab schools, how they manage these dilemmas in practice, and how the nature of particular dilemmas might connect to their management strategies. Given the multicultural and politically conflictive context of the 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 in a way that seem to hinder their mentoring practice. Preparation programs for mentors need to highlight awareness of mentors' own culture and that of their mentees in order to implement a culturally and politically responsive practice. (Contains 2 tables and 1 figure.)