One-to-One Computing initiatives are K-12 Educational environments where student and teacher have Internet-connected, wireless computing devices in the classroom and optimally at home as well (Penuel, 2006). One-to-one computing has gained popularity in several schools and school districts across the world. However, there is limited research exploring the barriers of implementing one-to-one computing, especially on a large scale. This study utilizes a qualitative approach by interviewing six senior administrators on identifying the barriers to implementing one-to-one computing. Solutions are recommended by the senior district leadership to help secure a successful and sustainable district-wide implementation of a one-to-one computing initiative. Results from this study have implications that could drive the planning of future initiatives in large school districts across the world.