Airways of postradiotherapy and postchemotherapy female oncosurgical patients on steroid therapy are devitalized and any airway handling in such patients commands caution. We report a case of a large iatrogenic tracheal rent occurring during manipulation of a flexometallic tube through a tracheostomy stoma created in a patient with postcricoid carcinoma undergoing esophagectomy and gastric pull-up surgery. The timely detection, emergent, and postoperative management strategies are discussed below.