Performing a probabilistic study rather than a determinist one is a relatively easy way to quantify the uncertainty in an engineering design. Due to the complexity and poor accuracy of the statistical moment methods, the Monte Carlo simulation (MCS) method is wildly used in an engineering design. In this work, an MCS-based reliability analysis was carried out for the stability of the chain pillars in the Tabas coal mine, located in Iran. For this purpose, the chain pillar strengths were calculated using the Madden formula, the vertical stress on the chain pillars was determined by an empirical method, and a numerical modeling was performed using the FLAC3D software. The results obtained for the probabilistic stability analysis of the chain pillars showed that the failure probability obtained for the designed pillars by applying the MCS method were approximately the same as that obtained by the advanced second moment (ASM) method, and the values obtained varied between 12 and 18 percent.