This chapter argues that the possibility of transformations and transformative experiences shows that strict, long-term punishments are epistemically irrational. Since the rationality of punishment must be sensitive to the mental states of the person being punished, including their mental states after the time of the punishable act, the possibility of radical changes makes it irrational to punish a person in a way that precludes considering future evidence about these changes. Since strict, long-term punishments, such as sentences of natural life without the possibility of parole, do just this, such punishments always run afoul of the demands of epistemic rationality.