Individuals with autism spectrum disorder (ASD) often have difficulty generalizing newly acquired communication skills to different contexts. In this study, a multiple baseline across settings (clinic, school, and home) design was used to determine whether an 8-year-old boy with ASD could learn to approach communication partners to request preferred items using an iPad®-based speech-generating device (SGD). Results indicated that the participant learned to approach communication partners to request across all settings. Acquisition of this skill was fastest at school and slowest in the clinic. The participant's learning generalized to a novel room within the same setting, and he was also able to retrieve the SGD prior to approaching the communication partner without additional teaching. Results suggest that individuals with ASD may benefit from being systematically taught to use an SGD across different settings and communication partners.