Former prisoners are at high risk of economic insecurity due to the challenges they face in finding employment and to the difficulties of securing and maintaining public assistance while incarcerated. This study examines the processes through which former prisoners attain economic security, examining how they meet basic material needs and achieve upward mobility over time. It draws on unique qualitative data from in-depth, unstructured interviews with a sample of former prisoners followed over a two- to three-year period to assess how subjects draw upon a combination of employment, social supports, and public benefits to make ends meet. Findings reveal considerable struggle among our subjects to meet even minimal needs for shelter and food, although economic security and stability could be attained when employment or public benefits were coupled with familial social support. Sustained economic security was rarely achieved absent either strong social support or access to long-term public benefits. However, a select few were able to leverage material support and social networks into trajectories of upward mobility and economic independence. Policy implications are discussed. © 2014 by the Association for Public Policy Analysis and Management.