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Aim: The management of anastomotic leak after sigmoid colectomy for diverticular disease has not been well defined. Specifically, there is a lack of literature on optimal types of reoperations for leaks. The aim of this study was to describe and compare reoperative approaches and their postoperative outcomes. Methods: We performed a retrospective cohort study using the NSQIP Colectomy Module (2012–2019) and single‐institution chart review. Patients with diverticular disease who underwent elective sigmoid colectomy were included. Primary outcomes were anastomotic leak requiring reoperation and management of anastomotic leak. Results: Of 37,471 patients who underwent sigmoid colectomy for diverticular disease, 1003 (2.7%) suffered an anastomotic leak, of whom 583 underwent reoperation. Of the 572 patients who were not initially diverted and underwent reoperation for leak, 302 (52.8%) were managed with stoma creation – 200 (35.0%) with colostomy and 102 (17.8%) with ileostomy. The remaining 47.2% underwent colectomy with reanastomosis, suturing of large bowel, and drainage. There were no differences in length of stay, readmission, or mortality between patients who underwent ileostomy or colostomy at reoperation (p > 0.05). Single‐institution analysis demonstrated that 100% of patients with ileostomies underwent subsequent ileostomy closure, compared to 60% of patients with colostomies. Conclusions: In patients who suffer anastomotic leaks after sigmoid colectomy for diverticular disease and undergo reoperations, ileostomy at the time of reoperation appears to be safe, with comparable results to colostomy. Ileostomies were more frequently closed than colostomies. When faced with a colorectal anastomotic leak, ileostomy creation may be considered. [ABSTRACT FROM AUTHOR]