This article explores how leadership and gender are constructed by women principals of schools located in communities of multiple deprivation in two provinces of South Africa. Analysis of interview data uncovers a hierarchy of goals related to establishing a school, recruiting and retaining learners, ensuring they are ready to learn, developing learning and enhancing their life chances. The pursuit of these goals entails actions which both challenge and sustain gender disadvantage and offer both gains and losses for learners. A highly complex relationship between the material conditions of the school community, gender construction, the South African context and the individual principal's history and characteristics is suggested. The article concludes that principals are both bound by and challenge the constraints of gender. It also suggests that heroic Anglophone notions of principals turning around schools in communities of multiple deprivation is a process of misrecognition which conceals the reality of the lives and possibilities for both principals and learners in schools in such locations.