This naturalistic inquiry explored the cultural impact of a historically Black independent boarding school on the social and academic experiences of four of its graduates who attended two traditionally White universities. The study examined two primary questions: (a) What factors from the historically Black boarding school assisted or hindered students' transition into traditionally White colleges and universities?, and (b) What impact does institutional climate and culture (Black and White) have in shaping graduates' perceptions of academic and social success? The research findings reflected the historically Black boarding school experience as playing a significant role in shaping graduates' academic and social self-concepts.