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A growing body of research shows that principal turnover is higher among people of racialized backgrounds (Meyer et al, 2020), associated with lower rates of student proficiency (Grissom & Bartanen, 2021) and often due to environmental conditions (Levin, Bradley & Scott, 2019). This study sought to explore the tenure experiences of Black leaders in the San Francisco Unified School District through semi-structured interviews with principals and assistant principals. In addition to race being a personal characteristic (Fairley-Ripple, 2012), we found that race impacts Black leader behaviors and responses to environmental conditions. By explicitly naming, interrogating and challenging white supremacy culture, the District’s leadership development program helped its African American participants challenge SFUSD as a racialized organization, also serving as an effective intervention.