While much is known about the educational, behavioral, and social needs of adolescents receiving school-based special education services, one critical domain, health literacy, has been largely unexamined. Given the impact of health and health management on the well-being of all persons, and the likelihood of additional challenges for students receiving special education supports, this study sought to examine and compare the health needs and transition preparedness of 341 adolescents with and without Individualized Education Programs (IEPs). Survey items were selected from widely used health literacy, health risk, and health related quality of life measures. Findings revealed that for students with IEPs, the risk for having limited health literacy was 128% higher than for their peers without IEPs. Students with IEPs were also significantly more likely to demonstrate risk across indicators of health related quality of life, health risk, and access. Limitations, research recommendations, and implications are addressed.