Tracheal rupture occurred in 7 of 174 (4%) patients undergoing laryngopharyngectomy with gastric transposition. Tracheal tears were classified as proximal if they involved the upper two-thirds of the trachea (five patients), or distal if they extended into the lower one-third of the trachea (two patients) and their clinical features and management analyzed. Predisposing factors, including prior radiotherapy (three patients) and preoperative tracheostomy (1 patient) did not influence the site or severity of tracheal injury. Proximal tears were detected incidentally in four patients, but in one patient, manifested postoperatively with subcutaneous emphysema and pneumothorax. Distal tears manifested dramatically with a ventilatory leak. Adequate access for repair of distal tears may necessitate a right thoracotomy while proximal tears may be sutured through the cervical incision. Gastric transposition alone did not prevent air leak in two patients. Postoperative complications included prolapse of the stomach and bilateral pneumothoraces in one patient. Close interaction between the surgeon and the anesthesiologist ensured a successful outcome in six patients. There was one mortality.