This review examines the development of students’ engagement with school and how it may contribute to future academic success and individual well-being in different social contexts. The review discusses the two main approaches of school engagement research: one examines students’ behavioral, cognitive, and affective engagement (North American approach), while the other examines study-related vigor, absorption, and dedication (European approach). This research shows that a high level of school engagement is positively associated with academic success, and negatively associated with students’ ill-being, such as depressive symptoms and burnout. High engagement with school also fosters several aspects of students’ well-being, such as positive emotions and life satisfaction. Moreover, several contextual factors, including parental affect, teachers’ support, and a mastery-oriented atmosphere in the classroom, promote students’ engagement with school.