Students with chronic and complex medical conditions often require assistive technologies in order to accommodate both physical and cognitive needs. Survivors of childhood cancer who are eligible for special education offer a lens through which to examine barriers to assistive technology assessment, acquisition, use, and support for students with health impairments. In this article, we examine literature that suggests that special education students with a history of cancer are unlikely to gain access to assistive technology, despite clearly demonstrated needs. We discuss assistive technology literature to determine research-supported steps schools can take to increase and improve access to assistive technology for students with chronic and complex medical conditions.