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This qualitative study explores six formerly incarcerated college (FIC) students’ mental health challenges experienced in high school to expose how unmet mental health needs significantly contribute to the school-to-prison pipeline. Drawing from transformative social-emotional learning (tSEL) and Critical Race Theory (CRT), the data uncovered a troubling truth: trauma, grief, and internalized pain among high school students frequently go unrecognized and misinterpreted as “trouble-making” behaviors, resulting in exclusionary disciplinary measures and perpetuation of the school-to-prison pipeline. These narratives highlight the need for schools to implement holistic, trauma-informed interventions, like tSEL, that prioritize mental health equity to prevent carceral trajectories. This research also demonstrates how engaging students as co-researchers, like in CBPR, can directly shape responsive and anti-carceral school-based mental health strategies.