As a sociocriminologist studying women’s prisons, I have contended that leisure needs to be rethought as a component of its environment and therefore as subjected to prisons’ functioning and goals (Marcoux Rouleau, 2020). In the following pages, I build on this to argue that despite its many benefits to incarcerated women and people in general, leisure has a limited capacity to fix that which is cracked and broken by the institution itself. Indeed, poverty, homelessness, victimization, and addiction are pathways to poor health and to criminalization, especially among women (Chesnay, 2016, 2017). Incarceration amplifies and creates issues with health and wellbeing, leading critical scholars to conclude that such problems are constitutive of the institution (Robert and Frigon, 2006). I infer that emphasis on leisure as the penultimate answer to poor health in prison does a disservice to incarcerated individuals, who are held accountable for improving their wellbeing while government responsibility is deflected, and discuss what practitioners, scholars, and advocate can do about this.