The glenohumeral joint is one of the most frequently dislocated joints and occurs with increasing frequency in collision and contact athletes, especially those in sports that repeatedly place the glenohumeral joint in a position of vulnerability. Nonoperative management of shoulder instability especially in young contact athletes results in unacceptably high recurrence rates; thus, early surgical stabilization has become commonplace. Surgical stabilization typically yields acceptable outcomes. However, recurrent anterior instability may occur following a previous stabilization procedure at rates of 7% to 12%. Recurrent glenohumeral instability represents a treatment challenge for orthopedic surgeons as it not only has the potential to result in subsequent surgery, therapy, and missed activity time, but also has been associated with long-term degenerative joint changes. Thus, recurrent instability requires close examination to determine underlying pathology leading to failure. Evaluation of underlying pathology requires consideration of patient activity-related factors, hyperlaxity and multidirectional instability, glenoid bone loss, glenoid track lesions, and other pathologic lesions. Revision surgical stabilization approaches include arthroscopic and open stabilization, as well as glenoid osseous augmentation procedures. Postoperative rehabilitation and release to sports and activity must be tailored to protect the shoulder from continued instability. Understanding that risk of recurrent glenohumeral instability and the risk factors associated with it are essential so that these factors may be mitigated and recurrent instability prevented.