Studies of chronically homeless adults have not adequately investigated the impact of adverse childhood experiences. The current retrospective, longitudinal study profiles the childhood experiences reported by 738 participants in an 11-site supported housing initiative and examines how their childhood profile is related to their homeless history, their psychosocial status before entry into supported housing, and their outcomes once enrolled in supported housing. A two-step cluster analysis revealed three childhood profiles: Relatively Numerous Childhood Problems, Disrupted Family, and Relatively Few Childhood Problems. Results found that participants with Relatively Numerous Childhood Problems were significantly younger when they were first homeless and had worse drug use before entry into supported housing than other participants. There were no differences in housing, substance use, or mental and physical health outcomes once participants were enrolled in supported housing. Prevention of homelessness should focus, to the extent possible, on individuals with extensive childhood problems.