Our objective was to develop a standardized measurement system to evaluate structural support site failures among women with anterior vaginal wall-predominant prolapse according to increasing prolapse size using stress three-dimensional (3D) magnetic resonance imaging (MRI). Ninety-one women with anterior vaginal wall-predominant prolapse and uterus in situ who had undergone research stress 3D MRI were included for analysis. The vaginal wall length and width, apex and paravaginal locations, urogenital hiatus diameter, and prolapse size were measured at maximal Valsalva on MRI. Subject measurements were compared to established measurements in 30 normal controls without prolapse using a standardized z-score measurement system. A z-score greater than 1.28, or the 90th percentile in controls, was considered abnormal. The frequency and severity of structural support site failure was analyzed based on tertiles of prolapse size. Substantial variability in support site failure pattern and severity was identified, even between women with the same stage and similar size prolapse. Overall, the most common failed support sites were straining hiatal diameter (91%) and paravaginal location (92%), followed by apical location (82%). Impairment severity z-score was highest for hiatal diameter (3.56) and lowest for vaginal width (1.40). An increase in impairment severity z-score was observed with increasing prolapse size among all support sites across all three prolapse size tertiles (p < 0.01 for all). We identified substantial variation in support site failure patterns among women with different degrees of anterior vaginal wall prolapse using a novel standardized framework that quantifies the number, severity, and location of structural support site failures.