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Mentoring programs may offer a promising approach to support young adults in the process of reentry. However, research on mentoring typically focuses on outcomes and not processes, thus limiting the ability to disseminate these programs more broadly. This case study examines an organization working to help formerly incarcerated young adults, to better understand how relationships with adult mentors alongside a weekly group “transformative mentoring class” aids in the process of reentry. Through observations, interviews, and document analysis, this study contributes to the field of education by developing an understanding of what mentoring looks like in the context of reentry and informing theories about informal learning and youth development more broadly.