This study aims to improve our understanding of the postsecondary impacts of high schools by investigating whether or not exposure to different high school contexts may explain academic performance once in college. Drawing on a sample of 3,750 participants from the National Longitudinal Survey of Freshmen, descriptive and multivariate analyses examine relationships between students' precollege characteristics, the high school context, and first year college grades. Results indicate that the quality of the high school infrastructure and exposure to violence at school--two operationalized dimensions of the high school context--affect first year college grades above and beyond precollege academic achievement and a variety of other background characteristics. Results also provide evidence of the conditional nature of these effects, where the high school context reinforces advantages of students with relatively greater economic resources prior to college. Implications for policy are discussed along with a call for a more holistic and interdependent perspective in examining the secondary-postsecondary nexus.