OBJECTIVE This study was part of a large multi-method inquiry designed to examine the service and support needs of adolescents with special health care needs who are transitioning to adulthood. METHODS A multiple case study methodology relying on life history was used to ascertain perspectives of the parents on the longitudinal events and factors in the lives of adolescents with special health care needs that shaped or currently influence adolescent transition to adulthood. Three informants were purposively selected to depict a range of health and socio-economic conditions. Long interviews were conducted and audiotaped and transcribed data were thematically and taxonomically analyzed. RESULTS Six major themes emerged in the analysis: (1) Begetting a service system, (2) Pathology or not pathology, (3) Educational stability vs. interruptions, (4) Role blurring of parents and providers, (5) Private life made public, and (6) Independence vs. burden. CONCLUSIONS The study revealed that, consistent with the literature, adolescents with special health care needs do not follow typical developmental sequences, although their needs and desires are no different than those of typical adolescents. The lives of the adolescents and their families are significantly influenced by the timing and nature of the diagnosis, the family's articulation with service providers, and the degree to which school systems are responsive to atypical adolescents. Implications for health providers and future inquiry are advanced.