Housing instability and incarceration have complex and consequential interrelationships. People within jails and prisons are disproportionately affected by homelessness. Likewise, people experiencing housing instability have high rates of involvement with the criminal legal system (CLS). Both populations have dramatically increased in the United States since the 1970s. Reforms related to housing and the CLS are increasingly centered in public discourse and policy discussions, with the two issues increasingly overlapping. In this chapter, we argue that collaborations between researchers and practitioners are crucial for increasing housing stability and decreasing interactions with the CLS. Strategies to address structural barriers can be furthered by communicating with policy makers and leveraging existing funding opportunities and initiatives. We begin by highlighting relevant research and data and then provide key recommendations. Our understanding of the relationship between housing and CLS involvement comes from research within correctional facilities and shelters, national and large multi-site studies, and qualitative studies on stigma, discrimination, and challenges with exiting homelessness. Such studies show the overlapping prevalence of housing instability and CLS involvement and the influence of criminalization, policies, and social norms.