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Anastomotic and rectal stump leaks are feared complications of colorectal surgery. Diverting stomas are commonly used to protect low rectal anastomoses but can have adverse effects. Studies have reported favorable outcomes for transanal drainage devices instead of diverting stomas. We describe our use of the Heald anal stent and its potential impact in reducing anastomotic or rectal stump leak after elective or emergency colorectal surgery. We performed a single-center retrospective analysis of patients in whom a Heald anal stent had been used to “protect” a colorectal anastomosis or a rectal stump, in an elective or emergency context, for benign and malignant pathology. Intraoperative and postoperative outcomes were reviewed using clinical and radiological records. The Heald anal stent was used in 93 patients over 4 years. Forty-six cases (49%) had a colorectal anastomosis, and 47 (51%) had an end stoma with a rectal stump. No anastomotic or rectal stump leaks were recorded. We recommend the Heald anal stent as a simple and affordable adjunct that may decrease anastomotic and rectal stump leak by reducing intraluminal pressure through drainage of fluid and gas.