There are a variety of technological and operational needs in conventional programs for training independent living skills that are not being addressed, or are being solved poorly. In this paper, we will explore the potential of virtual environment technologies for filling the training gap. Our goal is to specify operating guidelines, technological changes and a research agenda for the development of advanced systems to train individuals “handicapped” by their physical environment. To demonstrate how these guidelines may be implemented, we will describe a program currently under development for training individuals with cognitive impairments how to access public transportation services.