As the number of women more than the age 65 increases, so will the need for treatment of pelvic organ prolapse and the comorbidities that come with surgical treatment of an aging population gain significance. Colpocleisis is an option for women failing or refusing conservative prolapse management and not desiring sexual function. The advantages of colpocleisis are decreased operative time, low complication rate, and ability to use local or regional anesthesia. We report a case of a 95-year-old woman whose procidentia was treated with colpocleisis. Endometrial evaluation with dilation and curettage was performed at the time of colpocleisis. Postoperative course was complicated by pyometra necessitating total abdominal hysterectomy and bilateral salpingoopherectomy, leading to further complications including deep vein thrombosis, anemia, atrial fibrillation, and pleural effusions. Preoperative versus intraoperative endometrial evaluation may decrease the risk of developing pyometra after colpocleisis and, therefore, diminish the possibility of multiple complications.