People are not expected to do well while in prison. People often do not do well in prison. Prison research is replete with accounts of the harmful psychological, behavioral, and social effects of incarceration, but much less attention or acknowledgment is given to the people who do not experience these negative outcomes and perhaps even flourish while on the inside. This dissertation better understands who is doing well in prison, who is experiencing change for the better in prison, and how the prison experience impacts reflections on well-being in life through three separate studies. The first study uses a negative case framework to identify incarcerated men who are doing well by avoiding negative outcomes across a number of psychosocial and behavioral domains (e.g. mental health, coping strategies), as well as assesses what background and environmental characteristics are associated with those who are doing well behaviorally and psychosocially. The second study identifies individuals who are reporting improvement in their personal circumstances during the first year of incarceration and assesses the processes and events that are associated with reported improvements. Specifically, an equifinality framework is used to highlight the numerous pathways that can lead to a single positive outcome (e.g., reporting improvement in prison). A multifinality framework is also used to highlight the numerous outcomes that can be associated with a single life event (e.g., incarceration). The final study of the dissertation descriptively assesses life satisfaction, psychological flourishing, generativity, and meaning in life among a sample of incarcerated men, as well as assesses the correlates of high well-being during incarceration. Using data from The Arizona Living and Working in Prison project (studies 1 and 2) and the Enhancing the Prison Environment project (study 3), results from this dissertation reveal a sizeable portion of incarcerated people who are doing well while incarcerated via avoiding negative outcomes and experiences, experiencing change for the better, and reporting high levels of well-being.