Despite advances in the understanding of anterior shoulder instability, failure rates after open and arthroscopic surgery have been reported to be as high as 30%. In general, a successful operative outcome for patients with shoulder instability requires the surgeon to perform a complete preoperative evaluation, a thorough diagnostic arthroscopy to evaluate for concomitant co-pathology, and implement an effective postoperative therapy program tailored to the repair strategy. In addition to the Bankart lesion, the treating surgeon must be aware of other co-pathologies, such as the HAGL lesion, ALPSA lesion, and SLAP tears, that can occur in concert with capsular pathology and present as potential barriers to a successful outcome. This article focuses specifically on the pearls and pitfalls that are important to recognize in the preoperative workup, intraoperative evaluation, and arthroscopic surgery to optimize surgical outcomes for anterior instability.