Despite a growing body of turnover literature, much remains unknown about the factors predicting career transitional behaviors of school principals. To bridge this gap, we examined variations in principal, school, and district characteristics influencing administrator leaver and mover behaviors, using Hierarchical Generalized Linear Modeling. Our findings revealed that class size, support staff, parental involvement, teacher incentives, unionization, and many other district-level policies offset turnover, thereby contributing to retention. Furthermore, predictors of principal mover behavior differed from those of principal leaver behavior, suggesting that different forms of exit paths may need different policy tools to improve retention.