Tracheal resection and reconstruction for postintubation stenosis is successful in more than 95% of initial repair attempts. The most likely causes of anastomotic failure are anastomotic tension, local devascularization, and granulomatous foreign body reaction. Incomplete resection of areas of stenosis or malacia might also lead to postoperative airway compromise. A variety of systemic factors might contribute to poor anastomotic healing. Postoperative respiratory difficulty requires immediate evaluation. In a patient with recurrent tracheal stenosis, the airway can be managed with dilation, or a tracheostomy or T-tube can be inserted through the failed anastomosis. Patients who are candidates for reoperative tracheal resection and reconstruction can expect good or satisfactory results in 91.9% of cases. Preoperatively addressing the patient's risk factors for failing, and liberally employing release procedures to reduce tension on the anastomosis contribute to the success of a reoperative procedure.