Abstract For anterior instability with glenoid bone loss comprising 25% or more of the inferior glenoid diameter (inverted-pear glenoid), the consensus of recent authors is that glenoid bone grafting should be performed. Although the engaging Hill-Sachs lesion has been recognized as a risk factor for recurrent anterior instability, there has been no generally accepted method for quantifying the Hill-Sachs lesion and then integrating that quantification into treatment recommendations, taking into account the geometric interplay of various sizes and various orientations of bipolar (humeral-sided plus glenoid-sided) bone loss. We have developed a method (both radiographic and arthroscopic) that uses the concept of the glenoid track to determine whether a Hill-Sachs lesion will engage the anterior glenoid rim, whether or not there is concomitant anterior glenoid bone loss. If the Hill-Sachs lesion engages, it is called an “off-track” Hill-Sachs lesion; if it does not engage, it is an “on-track” lesion. On the basis of our quantitative method, we have developed a treatment paradigm with specific surgical criteria for all patients with anterior instability, both with and without bipolar bone loss.