Mobile devices provide a number of compelling features for learning and instruction. Clearly, these devices are becoming more and more popular. Arguably the most popular mobile device for education is the iPad. Multiple one-to-one iPad initiatives are cropping up around the United States. While interest continues to grow rapidly, the research and best practices for using these devices is not becoming available at the same pace. At the University of Hawaii–Manoa, we have implemented a one-to-one iPad initiative in a dual licensure (general/special ed) elementary teacher preparation program. Since Fall, 2013 we have been collecting and analyzing formative evaluation data on the initiative. In this paper we report our findings to date and provide practical guidance and suggestions based on those findings. This descriptive case report provides an insider glimpse into the challenges and opportunities that are coming to light.