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The underrepresentation of men of color (MOC) in US higher education and the growing disparities in their educational attainment has prompted much concern among policy makers and educators. The objective of this chapter is to address the comparative perspectives on equity and inclusion aim of the book by exploring why MOC are less like to earn a degree. We begin with a review of the contemporary literature on MOC and their academic transition to college in the United States. Next, findings from a longitudinal study that explored the early transitional challenges experienced by this population are presented. Results show the stark differences between high school and college in terms of faculty expectations, autonomous responsibility for academic coursework, and academic demands permeated early academic experiences of a group of MOC. Implications for practitioners are discussed.