While individuals returning from prison face many barriers to successful re-entry, among the most serious are the challenges they face in securing housing. Housing has long been recognized as a prerequisite for stable employment, access to social services, and other aspects of individual and family functioning. The formerly incarcerated face several administrative and de facto restrictions on their housing options; however, little is known about the unique instabilities that they face. We use a longitudinal survey of urban families to examine housing insecurity among nearly 3,000 urban men, including over 1,000 with incarceration histories. We find that men recently incarcerated face greater housing insecurity, including both serious hardships such as homelessness, and precursors to homelessness such as residential turnover and relying on others for housing expenses. Their increased risk is tied both to diminished annual earnings and other factors, including, potentially, evictions from public housing supported by Federal "one-strike" policies.