Pine species are a key social and economic component in Mediterranean ecosystems, where insect defoliations can have far-reaching consequences. This study aims to quantify the impact of pine processionary moth (PPM) on canopy structures, examining its evolution over time at the individual tree level using high-density drone LiDAR-derived point clouds. Focusing on 33 individuals of black pine (Pinus nigra)—a species highly susceptible to PPM defoliation in the Mediterranean environment—bitemporal LiDAR scans were conducted to capture the onset and end of the major PPM feeding period in winter. Canopy crown delineation performed manually was compared with LiDAR-based methods. Canopy metrics from point clouds were computed for trees exhibiting contrasting levels of defoliation. The structural differences between non-defoliated and defoliated trees were assessed by employing parametric statistical comparisons, including analysis of variance along with post hoc tests. Our analysis aimed to distinguish structural changes resulting from PPM defoliation during the winter feeding period. Outcomes revealed substantive alterations in canopy cover, with an average reduction of 22.92% in the leaf area index for defoliated trees, accompanied by a significant increase in the number of returns in lower tree crown branches. Evident variations in canopy density were observed throughout the feeding period, enabling the identification of two to three change classes using LiDAR-derived canopy density metrics. Manual and LiDAR-based crown delineations exhibited minimal differences in computed canopy LiDAR metrics, showcasing the potential of LiDAR delineations for broader applications. PPM infestations induced noteworthy modifications in canopy morphology, affecting key structural parameters. Drone LiDAR data emerged as a comprehensive tool for quantifying these transformations. This study underscores the significance of remote sensing approaches in monitoring insect disturbances and their impacts on forest ecosystems.