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School principals are essential for providing strong educational opportunities for students. Principal turnover can be very disruptive to students’ education and overall school improvement efforts and damaging to teacher retention and student achievement. Policymakers, district administrators, and school stakeholders are interested in improving the stability of school leadership. The literature shows that principal retention is related to conditions in five areas: working conditions, compensation, accountability, decision-making authority, and professional development. Building on this literature, this paper presents findings from a national survey of secondary principals and focus groups. In general, larger percentages of principals planning to leave reported adverse conditions across all five areas. Additionally, principals in high-poverty, city, and rural schools were more likely to experience challenging conditions.