W straps are important surface supporting components. When they cooperate properly with inner supporting components, such as rock bolts and cable bolts, they can enhance the supporting effects and bridging bolting units with integrity. Unfortunately, relevant studies regarding this topic have not been extensively reported. In this study, the failure characteristics of the W strap in the field are discussed and different types of distortion are proposed. Followed by the detailed failure patterns of the strap, a possible mechanism and solution are hypothetically put forward, which are then both numerically and experimentally verified. Afterwards, a loading apparatus capable of examining the mechanical behaviours of the strap is designed, which can similarly recreate the loading environment of the strap to the situation in the engineering field. By virtue of the designed loading device, a series of failure patterns of the bolting system are presented, and the distortion degree of the strap is evaluated using a 3D scanning method. The major findings in this study are as follows: 1) a domed face plate is better than a square domed face plate; 2) the existence of a hole beneath the strap in engineering applications can easily induce failure; and 3) cracked but compacted gravel-like roof strata beneath the strap may not cause damage to the strap-bolt supporting system. These ideas present new understandings in terms of the working conditions of W straps in coal mine roadway supporting systems, and the results can be referred to by practitioners.