Young adults with Autism Spectrum Disorder (ASD) face unique social skills challenges as they transition into independent living environments and seek fulfilling relationships within their communities. Research has focused on social education and interventions for children with autism, while transitioning young adults with ASD have received insufficient attention. The purpose of this multisite case study was to explore perceptions of school personnel related to the use of visual support system (VSS) technology and enhancement of social skillsets for young adults with ASD. Information processing theory and social learning theory provided the research framework. Research questions addressed perceptions related to the utility of VSS technology and social skills teaching strategies. Interviews were conducted with 11 special education administrators, teachers, and intervention specialists from 3 different programs in the United States. Data from interviews and field notes were analyzed using open, axial, and selective coding; themes such as social skills, video-modeling, learning strategies, use of visual technology, and cognition emerged. Participants indicated that exploring cognitive learning strategies underpinned with VSS technology provided alternative methods to teach social skills in classroom settings. They identified the need for more funding for VSS technologies for all learners. Implications for social change include that social skills and critical thinking skills can be enhanced by learning through the use of VSS technology. Empowering young adults with ASD to participate with greater confidence in learning situations and in social situations will support their efforts to be more comfortable and to interact more appropriately in work and community interactions.