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This paper explores prisoner-authored and produced newsletters as informal but powerful sites of critical pedagogy within carceral institutions. Drawing on Freire’s Pedagogy of the Oppressed, we analyze prisoner narratives from Out of Bounds, a Canadian prison publication, exploring how they articulate and complicate the lived realities of imprisonment. We argue that through dialogical storytelling, grounded experience, and problem-posing, these texts function as pedagogical acts, challenging institutional logics and resisting oppression. In contrast to formal prison education, often shaped by domination and control, prisoner-led publications offer a vital contribution to emancipatory education and learning. In the face of funding cuts and digital exclusion in prison education, peer-driven forms of critical knowledge construction demand recognition as legitimate and transformative interventions.