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A woman in her 80s with a history of three vaginal deliveries presented with an incarcerated 71 mm silicone ring pessary that had been retained for 6 months. She had been managed conservatively with pessaries for 8 years due to Grade 2 rectocele, with regular pessary changes every 4–5 months until this incident. She had no additional comorbidities. On initial examination, the pessary was immobile, with evident vaginal tissue fusion noted in the posterior fornix, indicating significant incarceration. No specific preoperative investigations were deemed necessary, and a clinical diagnosis of incarcerated ring pessary with vaginal adhesions was made.