In England and Wales, ‘punishment’ is a central element of criminal justice. What punishment entails exactly, however, and how it relates to the other aims of sentencing (crime reduction, rehabilitation, public protection and reparation), remains contested. This article outlines different conceptualizations of punishment and explores to what extent offenders subscribe to these perspectives. The analysis is supported by findings from two empirical studies on the subjective experiences of imprisonment and probation, respectively. Semi-structured interviews were conducted with 15 male and 15 female prisoners and seven male and two female probationers. Two primary conceptualizations of punishment were identified: ‘punishment as deprivation of liberty’ and ‘punishment as hard treatment’. The comparative subjective severity of different sentences and the collateral (unintended) consequences of punishment are also discussed. It is shown that there are large individual differences in the interpretation and subjective experience of punishment, which has implications for the concept of retributive proportionality, as well as the function of punishment more generally.