The purpose of this study was to document the process one district used to design, develop, and implement a one-to-one pilot at its high school as part of its broader commitment to contemporary learning. Specifically, this qualitative case study (a) outlines the process of the laptop pilot, (b) describes the pilot implementation experience for both teachers and students, and (c) shares the results of this pilot study that informed the district's next steps in its one-to-one initiative. Recommendations are also offered for other schools to consider when implementing a one-to-one pilot or program.