Understanding the developmental responsiveness of secondary school environments may be an important factor in supporting students as they make the transition from one school to the next. Students' needs may or may not be met depending on the nature of the fit between their basic and developmental needs and secondary school structures at the middle and high school levels (Deci & Ryan, 1985; Eccles & Midgley, 1989; Eccles & Roeser, 2011; Eccles et al., 1993). Continued research on secondary school structures and how middle and high school environments support students' needs is warranted (Caskey, 2011). Specifically, there is a need for research that investigates students for an extended period of time across school contexts to gain a more detailed understanding of how their needs are met within structured and unstructured aspects of both environments. Listening to the voices of those intimately involved in the middle-to-high-school transition, including students along with their teachers and school administrators, may help to extend the literature on how such environments are responsive to the needs of today's adolescents. The current qualitative, constructivist, multi-site case study focused on how students' needs are met within school environments as they make the transition from middle school to high school. (Contains 2 tables, 1 figure, and 1 footnote.)