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Although many high schools employ security guards, their relationships with students have received little attention. In this paper, I explore students' relationships with security guards in a large public high school near Chicago. I examine these relationships through the lens of “criminalized childhoods” (Dinsmore & Pugh 2021) in the context of the school-prison nexus (Meiners 2007). I use three years of ethnographic observations and data from 108 interviews to demonstrate how security guards operate both as agents of the school-prison nexus and as critical lifelines to students due to their cultural competencies and shared social statuses. In this way, I argue that security guards contribute to schools’ “refraction” of inequality (Downey & Condron 2016), challenging purely reproduction-focused perspectives of schooling.