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The vaginal pessary is a safe and effective method for the correction of uterovaginal prolapse. Complications are uncommon, but include fistula formation. We report a case of fistulous communication between the ureter and vagina that developed in a patient who had had a pessary for more than 8 years. She initially presented with urinary retention secondary to complete procidentia and declined surgical intervention. The patient was not compliant with follow-up. Eventually, she was scheduled for a vaginal hysterectomy and pelvic floor reconstruction, during which the communicating tract was discovered between the ureter and vagina. Ultimate treatment involved stenting of the ureter and interval ureteroneocystostomy. Fistulae can develop between the ureter and the vagina in the case of procidentia and a retained pessary.