This chapter enhances the understanding of the multifaceted challenges that individuals, especially older adults, seeking housing with a criminal background face. It reviews the ways in which individuals, especially older adults, can be vulnerable in terms of safety and security in their housing settings. Older adults may be particularly concerned about security and safety at home because their homes have been shown to be places where they can be victimized, either by telephone scams, door-to-door solicitation, bullying in age-congregate settings, and witnessing other crimes occurring in their residences. The chapter discusses ways in which forensic practitioners can support vulnerable populations, including older adults. It also discusses the complexities of affordable and safe housing using case examples and descriptions focusing on the older adult population. The chapter provides further recommendations on other areas of assessment and intervention that forensic social workers can conduct.