This study examined the student and high school contextual factors associated with high school students' enrollment in Hispanic-Serving Institutions (HSIs). The authors drew on a conceptual framework of college choice involving the concepts of multiple capitals and individual and organizational habitus to examine the postsecondary trajectories of high school graduates using the Educational Longitudinal Study 2002/06. Using hierarchical linear modeling, the authors analyzed two separate models. One model predicted enrollment in an HSI within the 2-year sector and one within the 4-year sector. Distinct predictors of HSI versus non-HSI enrollment were found, particularly for the 4-year sector. This study suggests that in both sectors, high school contexts had a significant effect of channeling students toward HSIs. (Contains 3 tables.)