Single-sex schooling for boys of color has become popular throughout the United States. Leaders and educators often consider these environments a school-based intervention to address adverse outcomes associated with Black boys. A contributing factor to these outcomes have been negative stereotypes of Black males related to Black masculinity norms, which developmental psychologists contend boys internalize during childhood. Interviews and observations were conducted over 12 months to describe a single-sex boarding program for first-grade African-American boys, affiliated with a coed independent school. Designed to facilitate boys’ positive identity development, the program’s mission and vision, educational philosophy, and schedule/programming will be primarily described from boys’ perspectives. The goal is to explore the merits of this single-sex intervention to ameliorate how Black male stereotypes and masculinity norms contribute to the school-to-prison pipeline.