The United States has experienced dramatic increases in both incarceration rates and the population of insecurely housed or homeless persons since the 1980s. These marginalized populations have strong overlaps, with many people being poor, minority, and from an urban area. That a relationship between homelessness, housing insecurity, and incarceration exists is clear, but the extent and nature of this relationship is not yet adequately understood. We use longitudinal, administrative data on Michigan parolees released in 2003 to examine returning prisoners’ experiences with housing insecurity and homelessness. Our analysis finds relatively low rates of outright homelessness among former prisoners, but very high rates of housing insecurity, much of which is linked to features of community supervision, such as intermediate sanctions, returns to prison, and absconding. We identify risk factors for housing insecurity, including mental illness, substance use, prior incarceration, and homelessness, as well as protective “buffers” against insecurity and homelessness, including earnings and social supports.