Today's students are digital natives. From computers to MP3 players, the everyday use of technology in society underscores the necessity of using technology in education. The use of digital simulations especially has had positive outcomes for students with disabilities in generalizing various life skills necessary for transition beyond high school. For students with disabilities, the need for transition planning and practice is critical (Individuals With Disabilities Education Act [IDEA], 1997). Simulations that represent real-world tasks and situations have a long history of successful use in developing skills (e.g., driving, vocational skills, life skills, functional academics, communication). Digital simulations can provide experiences in which the student takes an active role in facilitating a desired outcome using stand-alone computer software, a personal digital assistant (PDA) or smart phone, virtual reality (VR), digital video, or simulations via the Internet. Simulations allow students to explore and become familiar with a task and/or environment in context with little or no risk, and they offer the advantage of repeated practice to increase the probability that new skills can be generalized into real-world situations. (Contains 4 tables.)