As a community-based sanction, juvenile probation exemplifies the potential of both communities and families to make significant contributions in promoting positive changes among offending youth. Yet, surprisingly little research has explored the nature of these relationships and its association with offending. This study (1) examined the associations between youth–officer relationships, youth perceptions of parental support and knowledge, and probation non-compliance and (2) explored the role of parental support and knowledge as moderators of the association between youth–officer relationships and probation non-compliance among 110 youth supervised on probation (23 % females; 60 % African American). The findings showed that tough or punitive youth–officer relationships were associated with greater counts of technical violations, but fewer counts of delinquent offenses. Parental support was associated with fewer counts of delinquent offenses and parental knowledge was associated with fewer counts of both delinquent offenses and technical violations. These findings provide evidence to the important role of both parents and probation officers and underscore the potential benefits of parent–officer collaboration in facilitating successful interventions among offending youth.