The present study is organized around the central hypothesis that the high school context affects students’ postsecondary outcomes. Drawing on a nationally representative sample of high school seniors from the Educational Longitudinal Survey (ELS:2002), this study broadens our empirical understanding of how students’ acquisition of human, social, and cultural capital at the individual and school level affects 2- and 4-year college attendance. Results highlight the normative role of high schools in promoting college enrollment, particularly the role of socioeconomics, academic preparation, and access to parent, peer, and college-linking networks. This study advances our understanding of the secondary-postsecondary nexus and has implications for policies and practices aimed at realizing the current administration’s promise of providing greater access to postsecondary education for all students.