To identify factors associated with unsuccessful pessary fitting in a large cohort of patients with symptomatic pelvic organ prolapse (POP). This prospective observational study included 611 consecutive women with symptomatic POP in a tertiary-care hospital. Patients were initially fitted with a ring pessary with support. Those who failed were fitted with a Gellhorn pessary. A successful pessary fitting was defined as a patient who was fitted or refitted with a pessary and continued to use it 2 weeks later. Parametric and nonparametric tests were used for the data analysis. A total of 524 patients had successful pessary fittings (85.8% success rate). The success rate of the ring pessary with support was 57.9%, of the Gellhorn pessary was 69.1%. Stage IV prolapse (odds ratio [OR], 2.12), posterior compartment prolapse (OR, 1.92), genital hiatus (OR, 1.41), and vaginal introitus (OR, 1.40) were independent predictors of unsuccessful ring with support pessary fitting. Vaginal length (OR, 0.74/0.60 for ring with support/Gellhorn) and history of POP reconstructive surgery (OR, 2.50/2.58 for ring with support/Gellhorn) were independent predictors of both ring with support and Gellhorn pessary fitting. Stage IV prolapse, posterior compartment prolapse, large genital hiatus, and wide vaginal introitus were risk factors for unsuccessful fitting of ring pessary with support. Short vaginal length and a history of POP reconstructive surgery were risk factors for unsuccessful fitting of both pessaries.