PURPOSE OF REVIEW Cognitive disability places adolescents with special health needs at risk for poor health outcomes. Consequently, medical providers are faced with the challenge of deciding how to prepare cognitively impaired young adults for successful transition from child-centered to adult-oriented care. We provide a case example to illustrate this complex issue, describe research linking cognitive impairments to functioning in the context of chronic disease management, summarize current transition practices, offer recommendations to facilitate transition planning, and discuss how pediatric psychologists can assist this process. RECENT FINDINGS Concurrent cognitive impairments and pediatric chronic illness impose significant limitations on adolescents' self-care, disease management, and transition to adult care. There is also great variability in transition practices across pediatric centers, despite published transition guidelines, and little is known about how to develop successful transition planning for cognitively impaired adolescents. SUMMARY Transitioning cognitively impaired adolescents is a salient challenge in need of greater attention and further research. A multidisciplinary approach to transition that is tailored to the developmental, cognitive, and adaptive needs of this population can maximize the likelihood that transition will be successful.