My interest in critical leaderful educational practices emanated from my experiences as a researcher in a South African National Department of Education project that piloted the White Paper on "Inclusive Education Policy from 2001-2003" and in 2006 when I worked as a volunteer consultant with Twenty30, an independent, not for profit organization that works with schools in disadvantaged communities in Johannesburg, South Africa. Based on my work with the National Department of Education and Twenty30, in this paper I briefly sketch the profiles of Sunshine Primary and Dullsville Primary, two schools which operate within similar contexts of social fragmentation but which display two very different sets of behaviours. I sketch the legacy of racial segregation in South African schools and the resource infrastructural climate that characterized apartheid South African education. The sketch is meant to serve as a contextual background to understand the behavioural patterns of Sunshine Primary and Dullsville Primary in terms of how they negotiate the discriminatory apartheid script: one school which has resisted the negative script conferred upon it by apartheid and its legacy and the other school which has habitualized and internalized the debilitating script of apartheid engineering. Through reflection on the ethos of these two schools I conceptualized a proposed research project that I will conduct with a group of principals in Johannesburg, South Africa. The proposed study aims to explore how women school principals navigate the complexities of educational leadership in disadvantaged communities ravaged by HIV/Aids, poverty and child and woman abuse while also negotiating their status within the education fraternity that has historically relegated them to second-class citizenship. (Contains 5 notes.)