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Historically, education has played a central role in the lives of Blacks. Although Blacks continue their penchant for education, Black males have not fared as well in the educational pipeline. Data for this study emerged from a qualitative investigation of factors that promote success for academically underprepared Black males at a historically Black college and university (HBCU). Although all of the participants persisted to graduation, the participants discussed challenges that threatened to impede their academic success. This article discusses those challenges and outlines recommendations for the ways in which colleges and universities can work more effectively toward preventing attrition for Black males in higher education, particularly at HBCUs.