Objective: To investigate translabial ultrasound (TLUS) parameters that may predict failed pessary fittings in women with symptomatic pelvic organ prolapse (POP).Methods: All participants in this retrospective study presented to the Pelvic Floor Disease Diagnosis and Treatment Center (Liaoning Province, China) between May 2018 and December 2020 seeking treatment for symptomatic POP. Each had chosen vaginal pessary as first-line treatment, undergoing TLUS in advance of placement. Participants were grouped by outcomes of pessary fittings as successful or failed. Group-wise demographic and clinical characteristics, including TLUS parameters, were then subjected to uni-and multi-variate logistic regression.Results: A total of 373 women qualified for analysis, 255 (68.4%) achieved success, and were fitted with acceptable pessaries. Predictors of failed fittings included younger age (61.54 AE 10.25 y vs 64.72 AE 10.30 y; P ¼ 0.006), premenopausal status (14.4% vs 5.9%; P ¼ 0.006), sizeable hiatal circumference (20.36 AE 2.33 cm vs 19.70 AE 2.50 cm; P ¼ 0.02) and hiatal area (HA) (29.67 AE 7.14 cm 2 vs 27.27 AE 6.99 cm 2 ; P ¼ 0.003), levator ani muscle (LAM) avulsion (odds ratio [OR] ¼ 3.23, 95% confidence interval [CI] ¼ 1.62-6.46; P ¼ 0.001), enterocele (OR ¼ 2.51, 95% CI ¼ 1.11-5.68; P ¼ 0.03), and the inferiormost aspect of cervix situated below symphysis pubis (OR ¼ 0.52, 95% CI ¼ 0.29-0.95; P ¼ 0.03). In multivariate logistic regression, younger age (OR ¼ 0.98, 95% CI ¼ 0.95-1.00; P ¼ 0.04), sizeable HA on Valsalva (OR ¼ 1.04, 95% CI ¼ 1.01-1.08; P ¼ 0.02), LAM avulsion (OR ¼ 2.87, 95% CI ¼ 1.32-6.25; P ¼ 0.008), and enterocele (OR ¼ 2.70, 95% CI ¼ 1.12-6.50; P ¼ 0.03) emerged as independent predictors of failed pessary fittings.Conclusions: Younger age, LAM avulsion, enterocele, and sizeable HA on Valsalva proved independently predictive of failed pessary fittings in women with symptomatic POP.