Vaginal pessaries are commonly used in the conservative management of pelvic organ prolapse, and are generally viewed as safe alternatives to surgery. Serious complications are rare, but can and do arise, typically as a result of the pessary not being fitted and maintained correctly. This case describes delayed development of a vesicovaginal fistula (VVF) 8 months after vaginal ulceration was noted and the ring pessary removed. The 82-year-old patient was managed with a urinary diversion via ileal conduit. This case highlights the importance of meticulous follow-up when a pessary is removed in the setting of ulceration. It is the third documented case of a genitourinary fistula resulting from a vaginal ring pessary, and is the first reported case of this surgical technique being successfully used in this setting.