Examined psychological symptomatology in a community-based sample of 286 young adults with chronic health conditions randomly drawn from the rolls of two state programs for Children with Special Health Care Needs. The Psychiatric Symptom Index was used to assess mental health. We investigated how selected condition characteristics (e.g., indices of severity, symptom predictability, prognosis, age of onset, and visibility of condition) increased risk of psychological symptoms. Analyses indicate that (a) this population is at high risk for psychological symptoms, (b) selected risk factors (i.e., prognosis, restricted activity days, presence of hearing and speech problems, and perceived unpredictability of symptoms) have significant effects on mental health status when other variables are taken into account, and (c) respondents' perceptions of the impact of the condition mediates associations between selected risk factors and mental health. Results are discussed in relation to preventive interventions for this population of young adults.