This article explores how a single-sex school for boys of color intentionally and unintentionally (re)defines masculinity through rules and rituals. The school’s mission posits that boys become men through developing three skills: selfregulation, self-awareness, and self-reflection. Drawing from qualitative research data, I examine how disciplinary practices prioritize boys’ ability to control their bodies and image, or “self-regulate.” When boys fail to self-regulate, they enter
the punitive system. School staff describe self-regulation as integral to out-of-school success, but these practices may inadvertently reproduce negative labeling and control of black bodies. This article argues for school cultural practices that affirm, rather than deny, the benefits of boyhood.