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Women are less likely to hold leadership positions than men, and more likely to serve in more challenging positions. This study examines the relationship between district-level opportunity gaps and the likelihood of a district having a woman superintendent. Using data from New Jersey, we investigate whether women superintendents are more likely to be placed in districts with greater challenges, a phenomenon known as the “glass cliff.” We examine the relationship between superintendent gender and district-level opportunity gaps, finding women are more likely to lead districts with larger opportunity gaps. This research contributes to understanding the challenges women face in educational leadership and informs strategies to increase gender equity in school administration.