In this chapter we present some of the findings from a recent interview-based study of the professional biographies and values of a very large sample of senior managers currently working in prisons in England and Wales. Some of the questions we are asking ourselves are: can correctional senior managers be decent, liberal, humanitarian professionals ‘doing justice’? Under what circumstances, and at what points in history, has this been more or less the case? How are the tasks of punishing and ‘being humanitarian’ reconciled in a management role? The task we have set ourselves is not an easy one.