This study evaluated the effects of simulation training to teach functional community skills to four students with developmental disabilities in middle school. A multiple probe across participants and multiple probe across behaviors allowed for an evaluation of a functional relation between simulation and skill acquisition. Students learned how to match numbers from a shopping list to clothing sizes in a classroom simulation and then generalized this skill to community-based settings. Results are discussed in terms of a rationale for using computer based instruction and classroom simulation for teaching community skills and the potential for video and technology based solutions to augment traditional instruction. (Contains 3 tables and 3 figures.)