Stress-induced brittle fracturing near an excavation boundary results in a volume increase, known as bulking. Excessive bulking places added demand on the rock support, which, if not detected and addressed through preventative support maintenance (i.e., proactively added reinforcement), can cause the support to fail, leading to a safety hazard and costly production delays for underground mining operations. For caving mines, these project risks are exacerbated during cave establishment due to the large abutment stress from undercutting that redistributes and concentrates stresses near excavations critical for production. This paper reports the findings from research conducted to develop and improve geotechnical monitoring practices to support preventative support maintenance in deep mining operations. This research uses a unique geotechnical monitoring database collected for the Deep Mill Level Zone panel cave mine. The data was collected across a large footprint during the mine's ramp-up period and represents an initial step toward best practices for data collection at cave mines operating in high-stress environments. Borehole camera surveys supplemented by multi-point borehole extensometers have been used to determine the depth of stress fracturing in pillar walls as a function of the distance away from the undercut. Convergence measurements and LiDAR scanning are used to characterize the corresponding rock mass bulking. The results show that the interpretation of monitoring data can be used to identify the long-term depth of stress fracturing and bulking trends in response to undercut advances. These show that direct measures of stress-induced fracturing damage provide an early indication of excavations vulnerable to bulking and that LiDAR scanning is an effective method for capturing the onset of bulking and anticipating local areas likely to experience greater deformation demand as bulking progresses. Proactive and strategic geotechnical monitoring based on the long-term depth of stress-induced fracturing trends is proposed to assist with preventative support maintenance practices.