The extent of glenohumeral bone loss seen in anterior shoulder dislocations plays a major role in guiding surgical management of these patients. The need for accurate and reliable preoperative assessment of bone loss on imaging studies is therefore of paramount importance to orthopedic surgeons. This article will focus on the tools that are available to clinicians for quantifying glenoid bone loss with a focus on emerging trends and research in order to describe current practices. Recent evidence supports the use of 3D CT as the most optimal method for quantifying bone loss on the glenoid and humerus. New trends in the use of 3D and ZTE MRI represent exciting alternatives to CT imaging, although they are not widely used and require further investigation. Contemporary thinking surrounding the glenoid track concept and the symbiotic relationship between glenoid and humeral bone loss on shoulder stability has transformed our understanding of these lesions and has inspired a new focus of study for radiologists and orthopedist alike. Although a number of different advanced imaging modalities are utilized to detect and quantify glenohumeral bone loss in practice, the current literature supports 3D CT imaging to provide the most reliable and accurate assessments. The emergence of the glenoid track concept for glenoid and humeral head bone loss has inspired a new area of study for researchers that presents exciting opportunities for the development of a deeper understanding of glenohumeral instability in the future. Ultimately, however, the heterogeneity of literature, which speaks to the diverse practices that exist across the world, limits any firm conclusions from being drawn.