Weak shale roof falls have long been the main cause for fatalities in underground coal mines. Moisture-induced swelling is one of the root causes for the degradation of roof shales. In this study, slake durability tests are conducted on shale samples collected from Illinois basin coal mines, and different levels of durability are analyzed according to Gamble slake durability classification. There are two main mechanisms influencing the shape of retained fragments after two cycles of wetting and drying: mechanical abrasion and swelling pressure. A prototype optically based shale swelling apparatus is designed and manufactured for the shale free-swelling measurement. The experimental results suggest that swelling pressure tends to deteriorate shale laminations. Moisture-induced swelling of the No. 6 roof shale from Bear Run Mine was measured under 100% relative humidity condition. The measured swelling strain normal to beddings is ~5 to 7 times greater than the swelling strain parallel to beddings. This suggests that interlayer expansion plays a key role in moisture-induced swelling. Cracks induced by swelling pressure tend to occur along the bedding plane and lead to shale deterioration.