In an effort to increase both adolescents' engagement with school and academic achievement, school districts across the United States have created small high schools. However, despite the widespread adoption of size reduction reforms, relatively little is known about the relationship between size, engagement and outcomes in high school. In response, this article employs a composite measure of engagement that combines organizational, sociological, and psychological theories. We use this composite measure with the most recent nationally-representative dataset of tenth graders, Educational Longitudinal Study: 2002, (N = 10,946, 46% female) to better assess a generalizable relationship among school engagement, mathematics achievement and school size with specific focus on cohort size. Findings confirm these measures to be highly related to student engagement. Furthermore, results derived from multilevel regression analysis indicate that, as with school size, moderately sized cohorts or grade-level groups provide the greatest engagement advantage for all students and that there are potentially harmful changes when cohorts grow beyond 400 students. However, it is important to note that each group size affects different students differently, eliminating the ability to prescribe an ideal cohort or school size.