Background: Excessive glenoid retroversion is a known risk factor for posterior shoulder instability and failure after soft tissue stabilization procedures. Whether excessive glenoid retroversion is a risk factor for failure after posterior glenoid bone grafting is unknown. Purpose: To evaluate the biomechanical effectiveness of posterior iliac crest bone grafting (ICBG) for posterior shoulder instability with increasing glenoid retroversion. Study Design: Controlled laboratory study. Methods: Six fresh-frozen cadaveric shoulders had a posterior glenoid osteotomy allowing the glenoid retroversion to be set at 0°, 10°, and 20°. At these 3 preset angles, 4 conditions were simulated consecutively on the same specimen: (1) intact glenohumeral joint, (2) posterior Bankart lesion, (3) 20% posterior glenoid bone defect, and (4) posterior ICBG. Stability was evaluated in the jerk position (60° of glenohumeral anteflexion, 60° of internal rotation) by measuring (A) posterior humeral head (HH) translation (in mm) and (B) peak translational force (in N) necessary for translation of the HH over 25% of glenoid width. Results: At 0° of retroversion, the ICBG restored posterior HH translation and peak translational force to values comparable with those of the intact condition (P = .649 and P = .979, respectively). At 10° of retroversion, the ICBG restored the peak translational force to a value comparable with that of the intact condition (22.3 vs 24.7 N, respectively; P = .418) but showed a significant difference in posterior HH translation in comparison to the intact condition (4.5 vs 2.0 mm, respectively; P = .026). There was a significant increase in posterior HH translation and significant decrease in peak translational force with the ICBG at 20° of glenoid retroversion compared with the intact condition (posterior HH translation: 7.9 vs 2.0 mm, respectively; P < .006; peak translational force: 15.3 vs 24.7 N, respectively; P = .014). Conclusion: In this cadaveric study, posterior ICBG was able to restore stability to a level comparable to that of the native condition at 0° and to some extent at 10° of retroversion. However, posterior ICBG was not able to provide adequate stability at 20° of glenoid retroversion. Clinical Relevance: Posterior glenoid bone grafting with ICBG should be used with caution when performed in isolation in the setting of posterior instability associated with glenoid bone loss and combined glenoid retroversion of >10°.