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One major consequence of the tough-on-crime policies of the 1980s and 1990s was the “graying” of our prison systems. The ACLU estimates that by 2030, one-third of those in prison in the U.S. will be over the age of 50. Much of the research on reentry experiences, though, focuses on the experiences of those under 50 who do not face reentry challenges to the same extent as older formerly incarcerated individuals. Older formerly incarcerated individuals often experience greater levels of chronic ailments, physical disabilities, and mental illness as well as increased social care needs. This study explores how older formerly incarcerated individuals experience health and healthcare when released. Using in-depth interviews with 30 older formerly incarcerated individuals, we find that health and healthcare for this population is nuanced and dependent on other life domains. In particular, if the individual is old enough, accessing healthcare is easy due to Medicare. If the individual is not old enough to receive Medicare, accessing healthcare through insurance is often dependent on employment. At the same time, employment is often dependent on the individual’s health. The results from this study can help to inform reentry policy at the local, state, and federal levels.