Waste fills resulting from coal mining should consist of large, free-draining sedimentary rocks fragments. The successful performance of these fills is related to the strength and durability of the individual rock fragments. When fills are made of shale fragments, some fragments will be durable and some will degrade into soil particles resulting from slaking and inter-particle point loads. The degraded material fills the voids between the intact fragments, and results in settlement. A laboratory program with point load and slake durability tests as well as thin section examination of sixty-eight shale samples from the Appalachian region of the United States revealed that pore micro-geometry has a major influence on degradation. Under saturated and unsaturated conditions, the shales absorb water, and the air in their pores is compressed, breaking the shales. This breakage was more pronounced in shales with smooth pore boundaries and having a diameter equal to or smaller than 0.060 mm. If the pore walls were rough, the air-pressure breaking mechanism was not effective. However, pore roughness (measured by the fractal dimension) had a detrimental effect on point load resistance. This study indicated that the optimum shales to resist both slaking as well as point loads are those that have pores with a fractal dimension equal to 1.425 and a diameter equal to or smaller than 0.06 mm.