The purpose of this study was to examine whether secondary student engagement was predictive of college attendance. Data were drawn from the High School Longitudinal Study of 2009 9th grade (n = 21,444) and 11th grade (n = 20,549) cohorts. Multilevel modeling was used to analyze whether demographic, academic, financial, and engagement variables predicted postsecondary enrollment. Demographic (higher SES, attending a Catholic or private school) and academic (English and Math GPA) variables were predictive of college enrollment across both cohorts, as were participants' thoughts on the affordability of college. For ninth grade students, the engagement scales of family support for learning and future goals and aspirations remained significant predictors of enrollment after accounting for other variables. Among 11th grade students, peer support for learning, future goals and aspirations, and behavioral engagement remained significant predictors of enrollment. Student engagement is thought to underlie high school and college completion efforts but little research connects these levels of schooling. This study suggests providing support for students' engagement in high school could positively affect college enrollment. Financial education about the costs and options for paying for college may also be beneficial.