The number of middle level schools adopting 1:1 laptop programs has increased considerably during the past decade (e.g., Lowther, Strahl, Inan, & Bates, 2007; Storz & Hoffman, 2013; Texas Center for Educational Research, 2009). The cornerstone practices of the middle school concept (National Middle School Association, 2010), therefore, often serve as the backdrop for 1:1 implementation. The purpose of this qualitative study was to examine the intersection between 1:1 program implementation and the characteristics of effective middle schools associated with the middle school concept over a four-year period. Through ongoing participant observation, individual interviews, focus groups, and reviews of digital student work and documents, we explored the implementation of a 1:1 program by one middle school team that also espoused the middle school concept. We begin by providing perspectives on 1:1 programs and on the middle school concept from research and theoretical lenses. We then describe the qualitative methodology we employed to conduct this study. Next, we present an analysis of our findings, illustrating the opportunities, tensions, and trajectories that appeared when we examined 1:1 implementation alongside the characteristics of effective middle level schools. Finally, we explore the implications of these findings for middle level educators, school leaders, and other stakeholders as they adopt 1:1 programs in schools for young adolescents.