Mathematical problem solving is necessary in many facets of everyday life, yet little research exists on how to teach students with more severe disabilities higher order mathematics like problem solving. Using a multiple probe across participants design, three middle school students with moderate intellectual disability (ID) were taught to solve video-simulation real-world mathematical problems by finger counting using video prompting (VP) in conjunction with systematic instruction (e.g., least intrusive prompting) with error correction and feedback. The simulated videos covered a variety of thematic units (i.e., pet store, grocery store, household chores, sporting goods store, outside chores, and thrift store) students may encounter in their everyday lives. The results of this study demonstrated a functional relation between VP and participants' mathematical problem-solving skills. Findings from this study provide several implications for practice and research for using video-based interventions to teach mathematical problem solving to students with moderate ID.