Incarceration is definitively linked to poor health, and upon release from prison, many individuals experience difficulty in maintaining good health. Given the complexity of the reentry process, one's health status, both in and out of prison, likely influences additional aspects of reentry, such as abstaining from crime or adhering to parole terms. The purpose of this study is to determine whether in-prison physical and mental health, as well as changes to an individual's health upon release from prison, are related to the likelihood of recidivating. We employ the Serious and Violent Reentry Initiative (SVORI) data, a multi-state sample of formerly incarcerated males who are followed from prison to release into the community and interviewed about a number of post-prison release issues, including health. We use hierarchical logistic and multinomial regressions, where survey waves are nested within people, to assess if in-prison physical and mental health and post-release changes to health are associated with recidivism in two ways: general re-incarceration and re-incarceration due to either a technical violation of parole or a new conviction. With right-censoring due to recidivism or “failure,” our final sample size is 2180 person-periods (i.e., waves) nested within 871 respondents. We find that better physical health, both in-prison and changes in health post-release, is related to a higher likelihood of recidivating. Better mental health, both in-prison and changes to mental health post-release, is related to a decrease in the likelihood of recidivating. Individuals with poor mental health in-prison who make significant improvements after release see the largest reduction in their odds of recidivating. Finally, the combination of better mental health in-prison and increases in mental health post-release is associated with reductions in the likelihood of re-offending for both technical violations and new convictions. In sum, in-prison health continues to influence individuals after prison and is associated with their odds of recidivating, thus contributing to the churning of individuals through the prison system.