Abstract: The Housing First model is embedded in a supportive housing federal program aimed at reducing homelessness by offering housing vouchers and case management services to chronically unhoused veterans with co-occurring disorders. Despite the successes Housing First programs have achieved with the chronic unhoused population, including veterans, the cycle of homelessness continues to exist in this subgroup. These veterans have significant vulnerabilities, such as severe mental health and addiction histories, that contribute to their housing instability. The case narrative in this paper illustrates the story of a chronically unhoused veteran who cycled through episodes of homelessness due to ongoing substance use and evictions. On the veteran's third entry into a Housing First program, the social worker utilized the transtheoretical model (TTM) to evaluate the veteran's readiness to change and applied motivational interviewing (MI) principles to find a representative payee who would support housing stability, even if the veteran experienced a relapse. This approach can be considered harm reduction in supportive housing. Through the application of MI, the veteran exercised self-efficacy, opted for implementing a protective factor, and experienced long-term stable housing.