Management of vaginal prolapse in the elderly lacks a uniform consensus and continues to remain challenging. The authors report a case of an elderly lady who presented with a spontaneous vaginal evisceration. She had a long-standing vaginal prolapse being controlled by a shelf pessary, which, in her case became displaced 2 weeks prior to admission. The patient underwent a laparotomy with an intent to replace the bowel back within the peritoneal cavity and repair the vault. During the pelvic floor repair, she sustained an inadvertent button-hole injury to the rectum, which was oversewn. She went on to develop a rectovaginal fistula requiring a de-functioning colostomy. The patient made good recovery subsequently.