Various tools were designed to guide practitioners in the risk assessment of offenders, including the Level of Service and Case Management Inventory (LS/CMI). This instrument is based on risk assessment principles prioritizing the actuarial approach to clinical judgment. However, the tool’s architects allowed subjective judgment from the practitioners—referred to as clinical override—to modify an offender’s risk category under certain circumstances. Few studies, however, have examined these circumstances. Therefore, the current study used decision tree analyses among a quasi-population of Quebec offenders ( n = 15,744) to identify whether there are offenders more likely to be subjected to this discretion based on their characteristics. The results suggest that, although the override is rare, it occurred under few specific combinations of circumstances. More precisely, these findings propose that the utilization of the clinical override stems from a perceived discrepancy between risk prediction and management.