Non-compliance with a community-based sentence can result in serious consequences for an individual, including imprisonment. Probation officers, who supervise those on community sentences, play an essential role in supporting compliance and determining how to respond when non-compliance occurs; however, little research has explored how probation officers use their discretion. Neuropsychological dysfunction and a history of traumatic brain injury (TBI) are overrepresented amongst incarcerated offenders and associated with poorer outcomes (recidivism, treatment attrition, disciplinary infractions). However, much less is known about the neuropsychological function and history of TBI amongst community-based offenders (i.e., supervisees). Thus, this research project sought to understand probation officers’ perspectives on and responses to non-compliance and explore the association between a supervisee’s compliance and current neuropsychological functioning and recent TBI. The first study involved two focus groups with 17 New Zealand probation officers; the aim was to explore probation officers’ views on compliance and how they practice supervision. All probation officers reported using ‘social worker’ type, evidenced-based practices such as building quality relationships and using motivational interviewing. Probation officers viewed problems with cognitive skills as a key barrier to sentence compliance and reported using various strategies to support the compliance of supervisees with cognitive issues. The second study, involved 106 adult men (n = 82, 77.4%) and women (n = 24, 22.6%) on community sentences who participated in an initial interview that included a screen for a history of TBI and consent to collect compliance (arrests, sentence violations) and related variables (e.g., risk scores) from the New Zealand Department of Corrections database and police records over six months. At the conclusion of the initial interview, supervisees were invited to return and complete neuropsychological tests. Sixty-four men (n = 47, 73.4%) and women (n = 17, 26.5%) returned and completed the Repeatable Battery for the Assessment of Neuropsychological Status (RBANS), the Comprehensive Trail Making Test, and Color-Word Inference Test, and the Behavior Rating Inventory of Executive Function- Adult Version (BRIEF-A). Twenty-six probation officers, whose supervisees participated in the study, were interviewed regarding their supervisees’ compliance. The first manuscript from this study focused on the executive functioning of this sample compared to a normative sample and investigated the association between executive functioning and compliance with sentence conditions. The results indicated that the community-based sample had significantly poorer executive functioning compared to a normative sample. Still, contrary to what was expected, those supervisees who complied with their sentence conditions had poorer executive functioning than those who were non-compliant. However, exploratory analyses showed that those with poorer executive functioning received more probation officer support to comply with sentence conditions. The second manuscript described the sample’s neuropsychological function compared to a normative sample and investigated the association between sustaining a TBI in the last year (i.e., within the year prior to joining the study) and current neuropsychological function. We then explored if a TBI in the last year or current neuropsychological function were associated with compliance with sentence conditions and compliance with the law (i.e., being arrested). The results indicated that the community-based sample’s neuropsychological functioning was significantly poorer than a normative sample. Our findings also suggested that a TBI in the last year was a significant predictor of arrest, even when controlling for risk of reconviction and current substance use. However, a recent TBI was not associated with non-compliance with sentence conditions nor with poorer performance on the neuropsychological tests. In addition, no significant associations were found between performance on the neuropsychological tests and either measure of non-compliance. Overall, the results from this thesis suggested that individual characteristics like TBI and neuropsychological functioning impact compliance with a community-based sentence in different ways: A recent TBI was predictive of re-arrest while serving a community sentence, and poorer neuropsychological functioning was significantly associated with increased support from the probation officer to comply. The main implications of this research for corrections departments are that supervisees on a community sentence with poor neuropsychological functioning or a recent TBI may need additional monitoring or support to reduce the risk of non-compliance and reoffending. While further research needs to be undertaken to inform any changes in policy or practices, the results from this thesis suggest that community corrections would benefit from the implementation of services and screens to target important responsivity issues like TBI and poor neuropsychological functioning. Corrections departments attention to these issues may help alleviate the risk of individuals getting trapped in the criminal justice system for non-criminal activities (e.g., not attending an appointment).