In recent decades, the United States has seen the simultaneous rise of mass incarceration and homelessness. The two crises interact with and worsen one another. Mass incarceration and homelessness are driven by the same structural factors and exacerbate one another in a feedback loop. People on community supervision face many barriers to housing, putting them at high risk of experiencing homelessness in the months following release. People experiencing homelessness are at heightened risk of criminal justice involvement, including violating the terms of their community supervision, for engaging in survival behaviors in public spaces. This paper presents evidence-based approaches to improving housing strategies for reentry populations, preventing homelessness among those in community supervision, and rehousing members of the reentry community experiencing homelessness. It concludes with recommendations for policymakers interested in improving housing outcomes and overall reentry success for people on community supervision.