This study explores how middle-aged homeless persons in Atlanta, GA, who have harmful, self-identified addictive behaviors come to make positive material and psychological changes, while constrained by urban poverty and structural violence. This study is divided into two parts. In part one, I examine the interaction between individual, social, and material factors that promote recovery from addiction in a poor, urban context. I argue that recovery occurs through a process, initiated by a decision and realized through practice. Recovery is enhanced by a stable community and consistent material access. In part two, I examine how pain associated with homelessness can create a strong drive to intensify substance usage as a means to seek relief. I then describe how alienation, pain and corresponding addictive behaviors among homeless persons can be lessened through intentioned, empowering acts, which I call “symbolic love”. Finally, I offer policy recommendations based on my findings.