Whether through scaring incarcerated people straight or encouraging rehabilitation through treatment, most people hope that, one way or another, incarceration will alter an individual’s path towards a better life. Current forms of incarceration are not achieving this goal and instead inflict undue amounts of pain (Crewe, 2011; Sykes 1958). In times of deprivation and isolation, some people have found ways to not only persevere, but to thrive. Though these individuals are not commonly the focus of criminal justice literature, there is much value in shifting attention to people thriving in prison including the opportunity to gain knowledge on the multi-faceted nature of well-being broadly and the rehabilitation of incarcerated people more specifically. The current study uses structured interview data from 386 men serving time in a medium-security prison unit to explore the correlates of life satisfaction among people in prison. To identify contributing factors to well-being during incarceration, logistic and multinomial regressions analyze variation in the life satisfaction scores of these incarcerated men. The results from these analyses suggest that perceptions of life meaning, generativity, flourishing, and age are all positively associated with thriving in prison and frequency of experiences with incarceration are not related, positively or negatively, to life satisfaction. This study provides some support to current well-being literature and also introduces complexities to the existing knowledge regarding the relationships between demographics such as race or relationship status, and well-being.