This paper examines the effect of different geological and mining factors on roof stability in underground coal mines by combining field observations, laboratory testing, and numerical modeling. An underground coal mine in western Pennsylvania is selected as a case study mine to investigate the underlying causes of roof falls in this mine. Three-dimensional distinct element analyses were performed to evaluate the effect of different parameters, such as the variation of immediate roof rock mass strength properties, variation of discontinuity mechanical properties, orientations and magnitudes of the horizontal in-situ stresses, and the size of pillars and excavations on stability of the immediate roof. The research conducted in this paper showed that the bedding planes play an important role on the geo-mechanical behavior of roofs in underground excavations. Therefore, an appropriate numerical modeling technique which incorporates the effect of discontinuities should be employed to simulate the realistic behavior of the discontinuous rock masses such as the layered materials in roof strata of the underground coal mines. The three-dimensional distinct element method used in this research showed the capability of this technique in capturing the important geo-mechanical behavior around underground excavations.