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In 1996, Criminal Code amendments codified the principle of restraint while also offering a legislated statement of sentencing aims. However, sentencing policy often emphasizes the objective of deterrence (by imposing sentences of incarceration and mandatory minimum penalties, for example). The current study is an exploratory, qualitative analysis of the offender’s perspective on sentencing. Three aspects of sentencing are examined: 1) the purpose and objectives of sentencing; 2) the principles of sentencing; and 3) the sentencing process. Semi-structured interviews were conducted with offenders on conditional release from prison. The results indicate that offenders deny the deterrent effect of prison sentences. Yet, participant responses reveal that specific deterrence may be achieved in individual cases. Furthermore, judicial disparity (with respect to sentence length and sentence type) and consideration of individual circumstances impact offender perceptions of fairness at sentencing. These results suggest that consequentialist and retributivist rationales for punishment must both be sufficiently considered at the sentencing stage.