Developing special education programs that confer a free appropriate public education (FAPE) for students with disabilities has been a challenge for local education agencies since the Individuals with Disabilities Education Act (IDEA) was first passed in 1975. Developing a FAPE has been particularly challenging when students require assistive technology (AT) services or devices to meet their unique educational needs. In this article, we consider how students' individualized education program (IEP) planning teams have met this challenge by examining administrative and judicial rulings on the use of AT services and devices by students' with disabilities. Specifically, we first examine rulings from 2005 to the first half of 2013 regarding the IDEA, FAPE, and AT. Second, we explore how courts have interpreted the AT obligations of educational agencies with a focus on cases in which parents were the prevailing party. Primary reasons for school district losses in these cases include failing to: (a) provide AT assessments (b) address AT needs, (c) provide the AT devices or services specified in a student's IEP, (d) properly implement AT services. We end by discussing the implications of these court decisions for school districts use of AT services and devices with students in special education.