A concrete artificial side (AS) is introduced to stabilize a gob-side entry (GSE). To evaluate the stability of the AS, a uniaxial compression failure experiment was conducted with large and small-scale specimens. The distribution characteristics of the shear stress were obtained from a numerical simulation. Based on the failure characteristics and the variation of the shear stress, a failure criterion was determined and implemented in the strengthening method for the artificial side. In an experimental test, the distribution pattern of the maximum shear stress showed an X shape, which contributed to the failure shape of the specimen. The shear stress distribution and failure shape are induced by a combination of two sets of shear stresses, which implies that failure of the AS follows the twin shear strength theory. The use of anchor bolts, bolts, and anchor bars enhances the shear strength of the artificial side. When this side is stable, the components can constrain the lateral deformation as well as improve the internal friction angle and cohesion. When the AS is damaged, the components prevent the sliding of broken blocks along the shear failure plane and improve the residual strength of the artificial side. When reinforced with an anchor bar, the AS is still stable even after mining operations for three years.