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Street outreach is one of the most direct methods of engaging homeless individuals, but the characteristics of those most likely to be engaged this way is not well-understood. Data from the Department of Veterans Affairs (VA) Homeless Operations Management and Evaluation System showed that of the 70,778 literally homeless veterans engaged in VA homeless services in 2011–2012, 12% were through street outreach while the majority was through provider referrals (41%) and self-referrals (28%). Veterans engaged through street outreach had more extensive histories of recent homelessness, were more likely to be chronically homeless, and were more likely to be referred and admitted to the VA’s supported housing program than other veterans. These findings suggest street outreach is an especially important approach to engaging chronic street homeless veterans in services and linking them to permanent supported housing.