OBJECTIVE: This study aimed to determine factors associated with perceived comfort with pessary management among obstetrics and gynecology (OB/GYN) residents in the United States. METHODS: A 31-item anonymous electronic survey regarding experience with, attitudes toward, and comfort with pessary management was distributed to US OB/GYN residents in all postgraduate years (PGYs). Demographic and program-specific data on pessary education were collected. Descriptive statistical analyses were performed. Single-predictor logistic regression analysis, followed by analysis of a multivariable model that included significant single predictors, was performed to determine factors associated with residents' perception of comfort. Results were stratified for junior (PGYs 1, 2), senior (PGYs 3, 4), and chief (PGY4) residents. RESULTS: Four hundred seventy-eight completed surveys were returned and analyzed. Mean age of respondents was 29.5 (+/-2.56) years. Training levels were distributed evenly (PGY1, 25%; PGY2, 28%; PGY3, 25%; PGY4, 22%). Twenty-eight percent had a urogynecology fellowship in the department. Factors associated with comfort were similar for all training levels and included working with advanced practitioners, a formal urogynecology rotation, experience with pessary fitting, and receiving formal pessary-specific didactics (P < 0.001). PGY4s also benefitted from a formal urogynecology rotation. Factors that did not improve comfort were having a urogynecology fellowship and receiving general didactics on prolapse and incontinence. CONCLUSIONS: Gaining outpatient experience, especially with pessary fitting, along with formal didactics specific to pessary fitting and management may improve resident' confidence with pessary use.