Glenoid and humeral head bone deficiency is a common reason for recurrent anterior shoulder instability and failure of capsulolabral reconstruction. There is a strong association between the severity of the bone defects and the number and ease of recurrent instability. Clinical evaluation, advanced imaging, examination under anesthesia, and diagnostic arthroscopy are important in decision making. Glenoid bone loss greater than 20%, an engaging Hill-Sachs lesion, or Instability Severity Index Score greater than 6 are indications for an open bony procedure to restore the glenoid articular arc. Hill-Sachs lesions greater than 30% should be directly addressed with either an arthroscopic remplissage technique or open bone grafting procedure.