Transitional living programs (TLPs) are a housing intervention authorized by the Runaway and Homeless Youth Act to provide services for older youth experiencing homelessness. Preparing youth for independence is a chief program outcome for TLPs across the country. The findings of this qualitative study, with 32 former participants in TLP services, suggest that the primacy of this outcome may warrant reexamination. A dominant focus on the achievement of independence as a determination of program success does not (a) capture the most important roles TLPs serve from the perspective of youth and (b) account for the possible structural roots of youth homelessness in the United States that may prevent young people from maintaining stability after exit.