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The transition from high school to college is both challenging and stressful for most students—however, this transition is even more daunting for Black, Latine, first-generation, and low-income students. As research shows an increase in these students graduating from high school, there are still lower rates of college enrollment and persistence. These outcomes are further exacerbated due to persistent systemic disparities, policy trends, and inequitable K-12 school conditions. Considering these systemic and institutionalized inequities, researchers have found that pre-college programs as a tactic to improve college readiness for students of diverse backgrounds. Therefore, this qualitative study examined the experiences of first-generation, Black, and Latine, Upward Bound alums using their cultural capital to transition into and through college using photograph/artifact-elicited interviews.