A lack of multistep requesting among children with intellectual disability can be an indicator of complex communication and social challenges. This study aims to determine the effect of a systematic instruction (differential reinforcement, progressive time delay, and least-to-most prompting) using an iPad with the “GoTalk Now” app on the acquisition and maintenance of multistep requesting. Using a multiple-probe across-participants design, three children between the ages of nine and 10 diagnosed with intellectual disability participated in this study. The findings revealed that the intervention was effective in both the intervention and maintenance phases. In two participants, the change in performance occurred immediately, while in the other participant, it took more sessions to reach the acquisition criteria. Social validity data were obtained from participants’ teachers. Implications and future directions are discussed according to the findings.