This book provides a narrative account of the experiences of twenty former scholarship students from historically disadvantaged communities who attended elite public and private secondary schools. It draws on in-depth, one-on-one semi-structured interviews conducted with former scholarship recipients who were between the ages of 19 and 24 years at the time of the interviews. Various themes are explored, specifically focusing on elite schooling in relation to the experiences and navigational practices of the scholarship recipients and the adjustments that they felt they needed to make in order to fit into the elite school space.The book analyses and discusses the reflective experiences of students who were awarded a scholarship to attend an elite secondary school. It reveals that accepting the gift of a scholarship is far more complex, multi-layered, and at times harsh and even painful for the individual recipients than is possibly realized by those involved in this practice. This book contributes to academic educational debates within the sociology of education, elite schools and schooling in the post-apartheid South African context.