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Black communities in the United States have historically faced aggressive and heightened policing, criminalization, and incarceration compared with their peers. Black communities have also been denied equal access to safe and affordable housing. Together, the criminal legal system and the housing sector create a reinforcing feedback loop that traps people in a cycle of criminalization and homelessness. Due to historic and ongoing structural racism, Black people are disproportionately ensnared in this cycle, with serious consequences for community safety, public health, and civil rights. This paper provides a roadmap for understanding and dismantling the cycle of criminalization and homelessness. The first part documents how the criminalization-homelessness cycle has explicit roots in anti-Black racism dating back to slavery. The second part describes the present-day policies and practices that fuel each stage of the cycle, in which: police target people experiencing homelessness, criminalization leads to housing loss, and housing insecurity causes reincarceration. This section uses Atlanta, Georgia, as a case study to illustrate how the cycle operates in a major U.S. city with a large Black population, noting that the policing and criminalization of Black people experiencing homelessness is a longstanding problem in Atlanta. The third and final part presents evidence-based policy recommendations to invest in community safety and address the root causes of housing insecurity, rather than fueling a never-ending cycle of criminalization and homelessness. Additionally, this paper offers two major contributions to existing literature. First, it centers the experiences of Black people within the criminalization and homelessness conversation, and grounds this conversation in the long history of anti-Black laws used to police the movement of Black people in public space. Second, it examines Atlanta as a case study and presents original data analysis on racial disparities in arrests for vagrancy charges, as reported by the FBI, nationwide and then in Atlanta.