We report a case of a 66 year old male who presented with bleeding per rectum since 3-4 months. He had a history of being operated for hemorrhoidectomy 9 years ago. He underwent a colonoscopy which detected a large sessile polyp at the rectosigmoid junction for which polypectomy was done. The histopathology of the polyp revealed moderately differentiated adenocarcinoma arising within the villoglandular polyp (malignant polyp) with base involved. He was then operated for anterior resection followed by colorectal anastomosis. There was an anastomotic leak noted in the post operative period for which the patient was re-explored and Hartmans procedure was done in view of gangrenous sloughing of descending colon with resultant leak. 7 months later, patient was taken up for soma reversal and a covering ileostomy was done. He later followed up with an entire bowel wall coming out per rectum.It is a rare and poorly understood case of colonic mucosal sloughing out per rectum presenting without high fever, tachycardia, a rigid abdomen and hemodynamic instability.