School districts have been placed under increasing pressure to equalize student access to technology and equip students with the skills necessary to be competitive in a global economy. In response, a growing number of schools have sought an irreversible and dramatic departure from past practices, a second-order change, to learner-centered environments powered by one-to-one computing. While one-to-one computing has drawn the attention of researchers for more than 30 years, the field has not examined principals' experiences in leading the implementation of such an initiative. Yet leadership research continually affirms the importance of the principal in effective change implementation. This article discusses the findings of a study that explored principals' experiences leading the changes associated with a one-to-one initiative and the contexts or situations that influenced those experiences. Using a phenomenological method, this study explored how eight elementary school principals leading a one-to-one initiative viewed their role and responsibilities, promoted change, and responded to successes and challenges. This study provides new insights into change leadership that will inform practice in the leadership of one-to-one computing initiatives.