Many women suffering from Crohn’s disease or ulcerative colitis will ultimately require resection of some or all of the rectum with or without sphincter preservation because of medically refractory disease or a complication of their underlying disease such as severe proctocolitis, obstruction, dysplasia/neoplasia, or anorectal sepsis. This proctectomy procedure can be associated with its own complications during the course of the operation (e.g., injury to vital organs), early postoperative interval (e.g., superficial/deep surgical site infection, pelvic abscess, anastomotic leak), and late postoperative period (e.g., anastomotic fistula/sinus, entrapped ovary, infertility, sexual dysfunction, unhealed perineal wound). Many of these complications can be promptly diagnosed using cross-sectional imaging and endoscopic procedures and then readily managed with acceptable outcomes, especially with the assistance of other specialty physicians and surgeons. Unfortunately, no operation “cures” inflammatory bowel disease (IBD) and repeat procedures are commonly warranted for ongoing disease-related issues. It is therefore imperative that the involved surgeons consider several factors that are dictated by the individual patient, the behavior of their disease, and the specific disease- or procedure-related complication.