There are a number of community adjustment and transition models that indicate individuals with disabilities will require instruction across numerous domains that represent skills such as community literacy, mobility, purchasing, social interactions, and safety. To accomplish the instruction of such skills, community-based activities have been increasingly employed to teach these transition skills. However, the amount of time and the number of community-based learning trials needed for students with moderate to severe disabilities to acquire targeted skills can be in excess of the fiscal resources allotted. To overcome many of the logistical and fiscal problems associated with community-based instruction, educators have developed simulated activities that involve training in non-target environments with materials that simulate the targeted, or natural, settings. These simulated activities may or may not be successful depending on the attention given to strategies that promote generalization. These strategies are well known and have been extensively discussed in the literature. One method of instruction that can potentially expose learners to numerous stimuli designed to promote generalization of learned functional skills is computer-based multimedia. The purpose of this article is to identify and discuss the salient features of multimedia instructional tools that may be able to provide students with more effective and efficient simulated instructional activities in the area of transition skills. Also presented is information related to a federally funded project designed to develop a multimedia environment for providing this type of instruction as well as a vision for developing a research agenda designed to test the effectiveness of such instruction.