In this article, I explore the individual and systemic impact of hegemonic masculinity on college men serving as peer educators in sexual violence prevention programs. This ethnographic study was completed during the 2017-2018 academic year at a public university in the Southwest. Following an organization in the midst of a great deal of transition, I observed how hegemonic masculinity, particularly by way of male/men privilege and cisheteropatriarchy, was entrenched, actualized through curriculum, and occasionally resisted and critiqued. Through this article, I outline how the program allowed college men participants opportunities for further self-awareness around hegemonic masculinity, yet the program's systemic outcomes did not always play out in expected ways. Implications for future practice and research are discussed.