This study examines the approach of Victorian judges to the determination of sentence for an offender convicted of multiple offences. Given that a substantial percentage of criminal cases involve a multiple offender and that the majority of offences are committed by repeat offenders, the sentencing of such offenders is a matter of significant public policy interest. The study is based on qualitative interviews with a group of Victorian County Court judges, an analysis of sentencing data on rape, armed robbery and burglary from Victorian County Court records, and a legal review of High Court decisions and Victorian Court of Appeal decisions. The study examines the way judges apply the totality principle in sentencing multiple offenders; whether sentences imposed these cases conform to the principle of proportionality; and whether proportionality, in respect to the multiple offender, can be expressed as a detailed policy, with associated guidelines. The empirical work undertaken in this study indicates that there is a need to develop a more detailed and comprehensive set of sentencing principles and an associated numerical framework for guidance.