The use of long-Tendon ground support elements (cable bolts) is now a common practice in modern underground coal mines, hard rock mines, tunnels, and other underground structures. The paper briefly introduces the development of test methods for rock and cable bolts, including single-And double-shear methods, in the last 30 years and focuses on the novel development of the fourth generation of cylindrically shaped shear test apparatus (MK-IV Double Shear Box) for assessing tendon performance in shear based on the experience gained from the development of previous versions of shear experiment apparatus. The results were compared with similar test findings using a rectangular-shaped double-shear apparatus with and without friction across joint faces. The sequence of wire failure was studied by using the newly developed double-shear test apparatus, and the performance of abnormal phenomena in the double-shear tests was analyzed. The sequence of wire failure can be inferred based on the positive and negative values of strain gauge readings, and the wire of cable bolt under shearing may be broken in the joint area. The failure possibly occurred from one side to the other instead of from top to bottom. The modified double-shear test apparatus with a long section of concrete cylinder was proposed to conduct further research on cable bolt debonding.