This research is an investigation of one aspect of youth justice that is not as widely understood as it should be: probation. We know little about the types of conditions placed on young offenders and why certain conditions are used with certain offences. In addition, few studies have examined the principle of proportionality within probation. Related to conditions of probation is the charge "failure to comply with a disposition", which accounts for 13% of cases brought into youth court and 23% of cases sentenced to custody and are thought to be predominately breaches of probation. We do not know what unfulfilled probation conditions typically result in failure to comply offences. Finally, others argue that gender discrimination may be evident in the use of probation and failure to comply charges. The number of probation conditions appears to be significantly related to the nature of the first offence, whether or not there was a second offence and the length of the probation order. The investigation of failure to comply cases revealed that legal factors were significantly related to whether or not an offender would breach a certain condition of probation. The significance of gender was unclear in this analysis and requires further investigation. Both analyses revealed the need to explore the effect of extralegal factors, like the behaviour of youth court judges and police on probation. However, these data suggest that legal factors are significantly related to the sanctions used by judges and more generally have highlighted the importance of proportionality in sentencing.