Barriers in acquiring, maintaining, and generalizing daily living skills are factors that contribute to discrepancies in independent living outcomes among transition age youth and young adults with intellectual and developmental disabilities (IDD). Acquisition and generalization of daily living skills empowers transition age youth and young adults with disabilities to meet their own needs with minimal reliance on others. Infusing the use of technology as a self-prompting device facilitates the acquisition of tasks that may not be otherwise attainable. In this study, self-directed video prompting on an iPad with the My Pictures Talk application was used to help young adults with IDD in a postsecondary program acquire daily living skills in a single subject, multiple probe across subjects design. The effects of the intervention on generalization to tasks that were one, two, and three components different were also assessed. Results demonstrated a functional relationship between the introduction of the intervention and improvement in skill performance.