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Poor academic outcomes for incarcerated students have been well-established in the P-12 literature, yet little is known about their experiences with higher education. This qualitative study uses data drawn from interviews, observations, and field notes to address the research question: How do previously incarcerated youth describe facilitators and barriers to their academic success? Findings highlight that educators’ caring relationships with students are central to increasing the academic success of this population. Implications demonstrate that understanding how these students perceive their schooling experiences is imperative for creating community colleges better suited to meet the needs of this growing population.