Advocates of the middle school concept have long espoused the importance of being developmentally responsive to the unique nature and needs of young adolescents (National Middle School Association, 2010). As middle level schools strive to respond to the developmental needs of young adolescents, they should view students' technologies as an effective means to meet these needs. What happens when educators embrace and learn from young adolescents' preferred technologies as a way of engaging students? How and to what extent are middle grades students engaged in technology-rich classrooms? The purpose of this article is to provide a glimpse of the authors' six-year journey into middle grades students' engagement in student-centered, technology-rich classrooms. The authors begin by describing the engagement needs and expectations of "digital native" students (Prensky, 2001, 2010). They then describe the schools with which they have worked and the strategies they applied. Next they share student, teacher, principal, and parent perspectives, derived from interviews and ongoing participant observation. In particular, they highlight the attributes of technology integration that students find most engaging. Finally, they consider the challenges and opportunities that arise when implementing this kind of school change.