Recent studies of long-term imprisonment describe a largely invariant pattern of prisoner adaptation. This article, based on a qualitative study of men serving life sentences in England, argues that adaptation may in fact vary more than these studies imply, both because of the prisoner's age when sentenced, and because of the circumstances of particular offences. Participants engaged differently with the prison's rehabilitative 'offer', depending on how the sentence affected the life course, and what they understood to be the moral ramifications of the offence. These findings refine our understanding of adaptation, and suggest that a renewed focus on prisoners' moral reflexivity may bear fruit in future research.