Youth aging out of the child welfare system report high rates of unstable housing and homelessness which has been associated with problems including employment, education, health and mental health. This study used ethnographic data to examine a program providing subsidized apartments to youth aging out. The study sought to understand youths' and service providers' perceptions and experiences about the program. Receiving services and stable housing did not eliminate youths' struggles with employment, education, and mental health. Setbacks in even one domain often undermined their ability to maintain housing. Youths' stability and well-being were compromised by structural barriers such as housing quality, location of apartments, and access to transportation. Service providers face complex challenges while assisting youth aging out.