There are large inequalities in who enrolls in four-year collegiate programs, who finishes, and why. In this article, we draw on several waves of the Educational Longitudinal Study, explore family disadvantages, and uniquely highlight challenges first-generation students face. Family resources, cultural capital, and college-focused parental actions and their consequences for high school achievement explain most of the college attendance disadvantage. Inequalities in college completion, however, are notably also explained by disparate stressors, the need to work, and limited social/curricular integration while in college. We discuss these patterns and what they reveal about inequality and the limitations of contemporary college access.