This chapter addresses one particular debate in the penal theory literature: whether it is possible to reconcile proportionality with crime prevention and how a proper balance might be achieved between them. It is in two sections. The first looks at the theoretical questions and examines what might be learnt from the implementation of a supposedly deserts-based model in the Criminal Justice Act 1991. The second then draws on my own empirical work to explore the views expressed by magistrates, probation staff, offenders and victims on the underlying issues. A question that is pertinent in the UK context is how courts deal with prior record. Is taking an offender’s history into account consistent with a principle of proportionality or does it amount to covert incapacitative sentencing?