Purpose: To report the frequencies of surgical stabilization procedures performed by military shoulder surgeons and to use decision tree analysis to describe how bipolar bone loss affects surgeons’ decision to perform arthroscopic versus open stabilization procedures. Methods: The Military Orthopaedics Tracking Injuries and Outcomes Network (MOTION) database was queried for anterior shoulder stabilization procedures from 2016 to 2021. A nonparametric decision tree analysis was used to generate a framework for classifying surgeon decision making based on specified injury characteristics (labral tear location, glenoid bone loss [GBL], Hill-Sachs lesion [HSL] size, and on-track vs off-track HSL). Results: A total of 525 procedures were included in the final analysis, with a mean patient age of 25.9 ± 7.2 years and a mean GBL percentage of 3.6% ± 6.8%. HSLs were described based on size as absent (n = 354), mild (n = 129), moderate (n = 40), and severe (n = 2) and as on-track versus off-track in 223 cases, with 17% (n = 38) characterized as off-track. Arthroscopic labral repair (n = 428, 82%) was the most common procedure, whereas open repair (n = 10, 1.9%) and glenoid augmentation (n = 44, 8.4%) were performed infrequently. Decision tree analysis identified a GBL threshold of 17% or greater that resulted in an 89% probability of glenoid augmentation. Shoulders with GBL less than 17% combined with a mild or absent HSL had a 95% probability of an isolated arthroscopic labral repair, whereas a moderate or severe HSL resulted in a 79% probability of arthroscopic repair with remplissage. The presence of an off-track HSL did not contribute to the decision-making process as defined by the algorithm and data available. Conclusions: Among military shoulder surgeons, GBL of 17% or greater is predictive of a glenoid augmentation procedure whereas HSL size is predictive of remplissage for GBL less than 17%. However, the on-track/off-track paradigm does not appear to affect military surgeons’ decision making. Level of Evidence: Level III, retrospective cohort study.