Within the field of psychology there has long been debate, between researchers and opinion makers, on how important the relationship between clients and probation officer is, in determining probation outcomes. During the 1970s’ tough probation supervision practices emphasized surveillance, authority, and control to try to reduce re-offending. This management style prevailed despite the abundance of evidence to suggest such an approach did not work, rather it increased the likelihood of recidivism. Although these practices continue in some countries, in others a more responsive, and inclusive management style has become increasingly popular within probation officers. So, does a more responsive management style better support compliance? To answer this question, we utilised an existing dataset of 106 participants involved in “The Traumatic Brain Injury Project”. We interviewed probation officers to determine the quality of the relationship they have with their supervisees. Using a mixed method design we analysed the data to ascertain what factors, if any, had an impact on probation outcomes. Lastly, we identified individual client needs, such as trauma and substance abuse, to determine whether they have any bearing on sentence compliance. We found that the quality of the relationship between client and probation officer had no bearing on noncompliance outcomes. However, the acute factors recorded in a risk assessment tool at sentence commencement, although not predictive of non-compliance, had a bearing on probation outcomes for clients. Additionally, we found that a client’s complex needs, such as mental health or homelessness did not impact on sentence compliance.