The goal of this qualitative study was to demonstrate the achievements and failures of services that attempt to reach those most likely to be left out of the homeless-services delivery model—the chronically homeless street population. In 36 interviews with current and former chronically homeless street dwellers and the people who serve them, this study analyzed the service needs of chronically homeless street dwellers and the successes and failures of street-based medical and substance abuse services intersecting with the predominant continuum-of-care (CoC) model for homeless individuals, thus connecting chronically homeless street dwellers with services and housing. Using Grounded Theory as the guiding principle for analysis (Strauss and Corbin, 1998), the results of this study emphasize important differences between providers’ and consumers’ perceptions and theories on homelessness, service needs of homeless street dwellers, and service provision. Program and policy recommendations for ending chronic homelessness include the need to increase the affordable housing stock, enhance support systems for successful transition to housing and continuous support, and reduce bureaucratic barriers to housing.