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The glass cliff phenomenon describes women being hired into prestigious, but precarious, leadership positions. This study examines possible gendered sorting into “precarious” positions and subsequent turnover amongst superintendents in New Jersey. We examine longitudinal trends in the more than 600 districts in the state, finding that women are more likely to lead districts serving students qualifying for targeted supports, a measure of precarity, and new women superintendents are much more likely than men to turnover, with implications for superintendent hiring and support. We describe district contexts where men and women serve when entering, retaining, and leaving a position, as well as implications for recruitment, hiring, and support.