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Substance use disorders and related conditions play significant roles in urban homelessness and its personal and social costs. Traditional addiction treatment programs have failed to attract, engage, retain, and effectively treat this population, leaving homeless persons excluded from addiction treatment or constituting a chronically recycling segment of the treatment population. This paper describes the design and outcomes of the Journey of Hope Project—a special homeless initiative that was part of a broader “recovery-focused systems transformation process” in the city of Philadelphia. New approaches to outreach, treatment, and continuing recovery management demonstrated the ability to recruit, retain, and enhance long-term recovery outcomes for individuals with histories of severe substance use and related disorders and chronic homelessness. The service designs described and the service outcomes reported underscore the need to radically alter traditional service models to achieve enhanced long-term recovery outcomes with this population.