The concept of student engagement is critical in the discussion of school reform. This issue is particularly important in dropout prevention programs such as the alternative high school, although little empirical work guides intervention efforts. In this qualitative research, ethnographic observations were combined with interviews with 24 students and 12 teachers to examine how the offerings of the learning environment interact with the processes of engagement through the perspective of students in a high-functioning alternative high school. Youth narratives provide an account of the development of engagement in the context of supportive relationships and a caring school community. Findings suggest that affective engagement precedes school identification and behavioral commitments to learning. Their narratives aid in understanding how students construct stories of transition in the schooling process, and help to contextualize current theories that describe engagement in learning for youth placed at risk. (Contains 1 footnote.)