Anterior shoulder instability is a common orthopaedic problem, and the surgical treatment, both open and arthroscopic, has been shown to effectively restore stability and prevent recurrence. However, despite success with these surgical techniques, there are several clinically relevant complications associated with both open and arthroscopic techniques for anterior shoulder stabilization. These complications can be subdivided into preoperative, intraoperative, and postoperative and include entities such as nerve injury, chondrolysis, incomplete treatment of associated lesions, and subscapularis dysfunction. When they occur, complications may significantly impact patient outcomes and function. Therefore, surgeon awareness and identification of the factors associated with these complications may help prevent occurrence. Although failure of instability repair can be classified as a complication of surgery, it requires an entirely separate discussion and is therefore not addressed in this article. Because most of the previously published studies on anterior shoulder instability have emphasized surgical technique and clinical outcomes, the purpose of this article is to define the complications associated with anterior instability repair and provide recommendations on techniques that may be used to help avoid them.