The state of periodic loading and the interval of periodic roof weighting have an important role in geomechanical stability and, hence, in the continuity of longwall mining operations. In this paper, the mechanism of roof caving in longwall mining—together with the effect of engineering and geomechanical properties of surrounding rock masses on the magnitude and timing of periodic loading—is studied. For this purpose, a longwall mine is first modeled using Phase2 software, and then, by simulating the roof caving process, the periodic roof weighting intervals is calculated. Based on the numerical modeling, the first roof weighting interval and the periodic roof weighting interval are calculated as 27.2 and 12.1 m, respectively. Sensitivity analysis is then applied to determine the effect of changes in the mechanical properties of the rock mass, especially in the main roof and immediate roof. The results of the analysis show that as GSI and quality of the immediate roof increases, the periodic roof weighting interval also increases. Hence, the applied algorithm in this research study can effectively be utilized to calculate the periodic roof weighting interval in the longwall mining method.