Music and arts programs have increasingly been utilized to promote school engagement. Despite the fact that school engagement and music programs can be understood in myriad ways, little attention has been paid to potential distinctions between the types of music programs that underpin engagement. This article describes an investigation of how and when different types of school engagement were promoted through participation in a range of tailored music programs in four diverse school contexts. Four types of engagement were identified, including individuals' engagement in learning, peer engagement, connections with different members of the community, and community engagement. The characteristics of each type of program differed according to leadership approach, expectation of students, degree of student engagement, and structure. The benefits of tailoring each music program to meet the unique needs and interests of each school community are illustrated through these findings. Understandings of the relationship between music and school engagement are articulated.