Pillar design and stability analysis is an issue that is faced routinely in mining and civil industries. In mining operations, while the establishment of several mining levels is often necessary to ensure adequate production, it does result in formation of pillars that must be recovered under high stress conditions at later stages of excavation. Moreover, in civil infrastructures, such as underground power stations, waste repositories, warehouses, etc., design of remnant rock pillars is necessary and very common. Therefore, it is beneficial to develop guidelines that help in the design of rock pillars as well as to maintain their long-term stability. The aim of this paper was to delve into the mechanism involved in rock pillar loading process and failure mechanisms. The effects of pillar geometry, pillar and surrounding ground stiffness were investigated on pillar failure mechanism. A thorough numerical analysis was carried out to investigate the pillar deformation and failure process under natural loading conditions. Accordingly, the obtained results were compared against field data, from Canadian mining operations, published by various researchers. A fairly good match was obtained between the numerical findings and published field data.