Background: US military servicemembers experience higher rates of posterior and combined-type instability as compared with their nonmilitary peers. Purpose: (1) To determine the prevalence of glenoid bone loss (GBL) in young, active-duty military patients with combined-type shoulder instability who underwent operative shoulder stabilization; (2) to evaluate whether GBL is associated with differences in postoperative outcomes; and (3) to identify factors associated with larger defects. Study Design: Case series; Level of evidence, 4. Methods: This study included active-duty military patients who underwent primary surgical shoulder stabilization for combined anterior and posterior capsulolabral tears between January 2012 and December 2018. Preoperative magnetic resonance arthrograms were used to calculate anterior, posterior, and total GBL using the “perfect circle” technique. We recorded patient characteristics, revisions, complications, return to duty, range of motion, and scores on multiple outcome measures (visual analog scale for pain, Single Assessment Numeric Evaluation, American Shoulder and Elbow Surgeons, and Rowe). GBL prevalence was compared by time to surgery, glenoid version, history of trauma, and number of anchors used for labral repair. Outcome scores, return to active duty, and revision procedures were compared by degree of anterior or posterior GBL: <13.5% (mild) versus ≥13.5% (subcritical). Results: GBL was noted in 28 (77.8%) of the 36 patients. Nineteen (52.8%) patients had anterior GBL, 18 (50.0%) had posterior, and 9 (25.0%) had combined. Four (11.1%) patients had subcritical anterior or posterior GBL. Increased posterior GBL was associated with history of trauma ( P = .041), time to surgery >12 months ( P = .024), and glenoid retroversion ≥9° ( P = .010); increased total GBL was associated with longer time to surgery ( P = .023) and labral repair requiring >4 anchors ( P = .012); and increased anterior GBL was associated with labral repair requiring >4 anchors ( P = .011). There were statistically significant improvements on all outcome measures, with no changes in range of motion postoperatively. No significant difference on any outcome score was observed between patients with mild and subcritical GBL. Conclusion: In our analysis, 78% of patients had appreciable GBL, suggesting that GBL is highly prevalent in this patient population. Longer time to surgery, traumatic cause, significant glenoid retroversion, and large labral tears were identified as risk factors for increased GBL.