School psychologists are well-positioned to assist practitioners in engaging students in physical activity (PA) which can increase student access to improved well-being and associated health benefits. This may be of particular importance for adolescents with moderate to severe developmental disabilities (DD; autism and intellectual disability) who display various deficits in performing PA skills. Previous research suggests video-based instruction (VBI) effectively facilitated independence associated with PA skills in people with DD, however, additional research is warranted. The purpose of this study was to evaluate the degree a VBI impacted acquisition of skills in individuals with DD at school, and, subsequently, in a community setting. Multiple probe design was used to assess the effect of the intervention in four participants. The results indicate the intervention was effective in teaching three participants to perform the circuit in the school setting and transfer the skills to the community setting; however, maintenance was variable. Implications related to practice for school psychologists, teachers, and other practitioners, as well as, limitations and future research directions are discussed.