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Despite ample descriptive data about high international turnover rates of school principals, the factors associated with principal job dissatisfaction—and, distally, with higher leadership attrition—are inadequately understood. This limits the ability of schools, districts, states, and country-level institutions to understand why principals leave their jobs. This study examines how school climates are related to principal job satisfaction. The study uses hierarchical linear modeling on the Teaching and Learning International Survey to probe this association. Findings suggest ways that principal training and ongoing professional development programs can better support principals to remain in their schools.