The incidence of occlusive web following stapled anastomosis for curative resection of rectal cancer is unknown and the management of this entity not well defined. A 73-year-old patient underwent a double-stapled anterior resection with a temporary loop ileostomy for a T3,N1 rectal cancer. He received postoperative chemoradiation adjuvant therapy. Prior to ileostomy closure, sigmoidoscopy revealed an anastomotic occlusive web at 10-12 cm from the anal verge. Under monitored sedation, a flexible sigmoidoscope was inserted per anus and advanced to the level of the occlusive web. Utilizing hydrostatic balloon dilatation, the occlusive web was broken and the bowel lumen was restored. The procedure was performed expeditiously and without complications. Subsequently the patient underwent ileostomy closure and experienced normal bowel movements. Although occlusive webs are uncommon after colorectal anastomosis, this case report describes a safe, effective, and uncomplicated endoscopic procedure that can be performed in patients with anastomotic occlusive web developing after prolonged fecal diversion.