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The current paper introduces a conceptual model of historically underserved student success in higher education. The model integrates Perna and Thomas’s (2008) multi-layered theory of student success with analogous features of the social ecology of human development to elucidate the barriers underrepresented students cope with, and the conditions under which students can be successful. Focusing on a sample of City University of New York (CUNY) students, findings from a survey analysis indicate that while support factors like self-efficacy and positive campus interactions benefit many students, they often have less favorable effects on the most disadvantaged, leading to higher stress and lower academic performance. The need for more targeted interventions to support historically underserved students is discussed.