This study used a phenomenological study design to better understand the influence of school environments and structures upon student engagement. Data were collected using semi-structured interviews and researcher memos, and analyzed using the methods established by the design model of Interpretative Phenomenological Analysis (IPA). The study focused understanding teacher perceptions and understandings of student engagement and the practices and structures that engender it. Participants included eight members of a middle school faculty from a small, urban, independent school located on the Upper West Side of New York City. This study used stage-environment fit and positive youth development to help answer the following question: How do middle level teachers in a small, urban, independent school understand the role of the environment in fostering student engagement and motivation?Secondary questions focused specifically on the way these participants defined and understood student engagement and strategies and structures that foster student engagement.Findings from this study reinforce previous research findings demonstrating a lack of fit between the unique needs of young adolescents and the structures and environments of traditional secondary schools. The study makes an important contribution to the literature in its assessment that those working with young adolescents must first unlearn the traditional perceptions of secondary education. Findings suggest that environments and strategies that most effectively engage young adolescents (1) promote close relationships between teachers and students built on trust and care, (2) value the voices and identities of every individual student, and (3) stand in contrast to the traditional conceptions of middle school educations.Recommendations include establishing curricula that offer the opportunity to value and capitalize on student voice and autonomy, hiring and retaining diverse faculty who put the needs 3 of their students first, and re-evaluating the traditional practices of instruction and assessment almost universally employed in middle level education.