Schools are not only tasked with communicating academic knowledge to students, but also preparing and training them to assume adult roles, including participation in the work force. Educators attempt to foster engagement with learning and cultivate student behaviors such as punctual attendance and preparation for classes, attention to lectures and directions, and timely completion of assigned tasks. These learning behaviors are crucial to students' success in school and their preparation for the labor market. However, the widespread practice of grouping students by perceived ability means that students in the same school, or even the same classroom, can have very different training experiences. While there is a large literature on how ability grouping can affect student achievement, we have comparatively little empirical evidence on how it affects the development of students’ academic engagement. I consider two different types of grouping – within-class grouping in the early elementary grades, and between-class grouping (tracking) during high school – using data from the Early Childhood Longitudinal Study Kindergarten Cohort of 2002 and the National Education Longitudinal Study of 1988. I describe predictors of students’ assignments to ability groups and examine opportunities for advancement. I also use propensity score stratification to estimate the effects of group assignments on math and reading achievement as well as students’ academic engagement through its attendant learning behaviors. Findings indicate that there are substantial opportunities for students to move up to higher groups as they progress through school and students can improve their group assignments by demonstrating positive academic engagement. However, group assignments do tend to “stick” to students over time, even after controlling for prior achievement, learning behaviors, and other observable characteristics. Moreover, assignment to a higher group improves students’ math and reading achievement outcomes and improves students’ academic engagement, while assignment to a lower group depresses both of these, making upward mobility more difficult. These effects diminish in size as students age. Following high school, students who graduated from an academic track were more likely to attend traditional four-year colleges (though less likely to attend other postsecondary education programs), and differences in labor market outcomes were modest.