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This study explores how formerly incarcerated adults make sense of the relationship between their experiences with punitive school discipline and their incarceration in Puerto Rico. Through Freirian dialogue circles, participants worked on a collaborative project that engaged their reflections on their journeys through both of these systems, highlighting points of overlap and outlining recommendations for stakeholders committed to creating schools that protect youth from criminalization and incarceration. Preliminary findings reflect frequent experiences of carceral school discipline, pointing to the existence of a school-prison nexus (Meiners, 2011). Given Puerto Rico’s status as a colony and historical efforts of hegemonic imperialist expansion through schooling (Stokas-González, 2015), I argue that carceral logics present in this context are inherently a manifestation of coloniality (Maldonado-Torres, 2016).