Over the past decade, there has been an increase of 1:1 laptop schools across the United States. Yet, minimal research exists which examines the experiences of school site administrators as they lead the implementation of a 1:1 laptop school initiative. This case study investigated the roles of principals and assistant principals leading 1:1 laptop schools and how this initiative influenced their leadership practices. A total of eight principals and five assistant principals were interviewed. One hundred twenty-nine teachers participated in an online survey. Findings revealed these school administrators played three significant roles: (1) promoters for risk-taking instruction with technology; (2) models of 1:1 laptop use and (3) stewards of best 1:1 laptop instructional strategies. Leading such schools also caused them to (1) experience a paradigm shift on how teaching and learning could look like in the classroom; and (2) compelled them to reevaluate and improve their leadership practices. As school site administrators consider leading 1:1 laptop schools, they must be prepared for unexpected changes in how teaching, learning, and leading are to be established. Research that examines how school administrators create a culture of risk-taking with technology and how it impacts instruction is recommended.