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The tough-on-crime policies of the 1980s and 1990s has resulted in the “graying” of our prisons. By 2030, one-third of those in prison in the U.S. are expected to be over the age of 50. Much of the research on reentry, though, focuses on the experiences of those under 50 who do not face reentry challenges to the same extent as older formerly incarcerated individuals. This population specifically struggles with employment and financial stability not only due to their past criminal record, but also because of their age as well as a possible disconnect between their skills, their health, and potential job opportunities. Using in-depth interviews with 30 older formerly incarcerated individuals, we find employment is interdependent with health and relates to other life domains as well, such as family reunification and housing. Depending on their personal circumstances, individuals may be overqualified for available jobs or lack appropriate marketable skills. Financial stability may also be affected by whether or not the individual qualifies for social security, has retirement funds, or has other resources such as savings or family support. The results from this study can help to inform reentry policy at the local, state, and federal levels.