One useful strategy to support students with intellectual and developmental disability (IDD) to promote appropriate behaviors across environments and gain the social skills is using social stories. In addition, experts have recognized iPads and apps were associated with less challenging behavior and more academic engagement over traditional materials (Lee, Lang, Davenport, Moore, Rispoli, Meer, & Chung, 2013). The focus this study was to examine the effectiveness of an intervention package featuring social stories delivered via an iPad and simultaneous prompting on frequency of targeted challenging behavior and comprehension of the social story of a student with IDD. A single-subject multiple probe across behaviors (Kennedy, 2005) design was used to investigate the effectiveness of this intervention on the student's ability to correctly match pictures to steps in social stories as well as the targeted challenging behaviors. The results, future research, and the limitations of the study are discussed.