This article provides insight and information about obstacles adolescents with special health care needs (ASHCNs) face as they progress to adulthood. Descriptions of these challenges are based upon clinical experiences in providing transition services to youth by the service coordinator seen through the Creating Healthy Futures transition clinic. These obstacles were classified as those related to health care, employment, education, independent living, social and recreational skills, and the service system. Information is also provided on the strategies project staff developed to assist youth in dealing with the challenges of the transition obstacles they faced.