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The assistant principal role is a steppingstone to the principalship. However, little is known about why some APs aspire to the principalship while others wish to remain in the role. We use data from Tennessee to explore the extent to which APs’ personal, principal relational, school, and professional factors predict their likelihood of aspiring to the principalship. We find that less experienced APs are more likely to aspire to the principalship and that tapping by their principals is highly predictive of their aspirations. We find that female APs are less likely to aspire to the principalship and Black APs are more likely to seek the principalship. Results have implications for how principals and districts support APs along the school leadership pathway.