Despite the advances in the surgical techniques and technology in colorectal surgery, the development of rectal anastomotic stricture is a common problem. In some case series, the incidence is estimated to be as high as 30%. Some of the known risk factors for developing a stricture include anastomotic leak and ischemia. Treatment options range from frequent dilations using digital rectal examinations and dilators if the stricture is low or endoscopic balloon dilations for higher strictures. Unfortunately, multiple sessions are typically required to achieve adequate results. We present a case report of a benign anastomotic stricture and describe a novel approach, transanal stricturoplasty, for this challenging problem.