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Objective: Our primary objective was to evaluate the proportion of women who underwent surgery after successful pessary fitting for pelvic organ prolapse (POP). Our secondary objectives were to assess when surgery occurs and to evaluate factors associated with choosing surgery as compared to continuing with a pessary., Methods: Our study population included women successfully fitted with a pessary for POP 1/1/12 and 12/31/16. We excluded non-English-speaking women and those who used pessary only as a bridge until surgery. We evaluated events occurring after a successful fitting, including whether women (1) continued pessary use, (2) underwent surgery, or (3) discontinued pessary without surgery. Our primary outcome was the proportion of women who opted for surgery after a successful pessary fitting for POP. We also assessed the median time to surgery and compared women who underwent surgery with those who continued with a pessary to assess variables associated with surgery., Results: Of the 444 women with POP who were successfully fitted with a pessary and met inclusion criteria, 137 (31%) ultimately underwent surgery. The median time to surgery was 10 months (interquartile range, 4-18), with 59% having surgery within 1 year, and 89% within 2 years. In a logistic regression analysis controlling for age in decades, advanced POP stage, and Charlson Comorbidity Index, younger age remained significantly associated with surgery (odds ratio, 0.77, 95% confidence interval, 0.62-0.95; P = 0.02)., Conclusions: Among women successfully fitted with a pessary for POP, one third ultimately underwent surgery, with approximately 60% of these women undergoing surgery within the first year and 90% within 2 years.