This qualitative case study examined school leaders' roles, perceptions, and challenges leading a one-to-one (1:1) laptop initiative in a coeducational, independent middle, and high school in the United States. The findings revealed how the school leaders led the school's 1:1 laptop initiative through collaborative, yet differentiated roles and responsibilities. Together, they established the school's vision, planned and implemented the initiative, supported teachers and students, reflected on their practice, and made changes as needed. Generally, the school leaders regarded the 1:1 laptop initiative as having a positive impact on teaching and learning by increasing student collaboration and access to information, as well as fostering teachers' reconceptualization of their practice. However, the impact on student achievement was inconclusive; they explained it was too early to gauge its impact. Challenges the school leaders experienced involved limited bandwidth, printing problems and students' off-task behaviors. They addressed them as they would any nontechnology challenge through problem-solving, shared decision-making, and fidelity to the school's mission and goals.