When considering the management of shoulder anterior instability with glenoid bone loss ≥25 % of the inferior glenoid diameter (inverted-pear glenoid), the consensus among recent authors is that glenoid bone grafting should be done. Although the engaging Hill-Sachs lesion has been recognized as a risk factor for recurrent anterior instability, there has been no generally accepted methodology for quantifying the Hill-Sachs lesion taking into account the geometric interplay of various sizes and various orientations of bipolar (humeral-sided plus glenoid-sided) bone loss. Keeping the glenoid track concept in mind, if a Hill-Sachs lesion engages the anterior glenoid rim, with or without concomitant anterior glenoid bone loss, it is possible to manage this pathology, reducing the risk of recurrent shoulder instability after surgery. If the Hill-Sachs engages, "Remplissage" or "Latarjet" surgical procedures are indicated depending of glenoid bone loss.