Disability law and technology services share a rich history. This article investigates this transformative relationship through the contextual framework of the Individuals with Disabilities Education Act. A summary of legal cases, accommodation services, and barriers to access are explored. This includes an overview of the challenges facing technology as we develop the classrooms of the 21st century. A reflection of past rulings, technological advancements, and ongoing questions culminates in a look at where special education technology is heading.