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This phenomenological study explores the types of challenges formerly incarcerated students identify as being the greatest barriers to maintaining a positive student experience while enrolled in a college-in-prison program. It contextualizes participants’ experiences within a framework of “college student thriving,” a construct which identifies key components of student success within academic, psychological, and interpersonal dimensions. Using thematic analysis and following a descriptive phenomenological approach, preliminary findings indicate that the greatest challenges experienced by students often relate to a lack of study space and research materials, friction with prison staff, and anxiety due to concerns regarding their own academic standing. Implications of this study can help educators and administrators more deeply understand student experiences within such programs.