The management of well differentiated thyroid cancer invading the trachea can be challenging. Invasion tends to occur in older patients in whom the well differentiated tumors may have acquired a more aggressive phenotype. It is generally agreed that longer survival and better control of symptoms are obtained if the gross thyroid tumor is fully removed. Resection of thyroid cancer that invades the airway is done: 1) to relieve or prevent airway obstruction, 2) to prevent death by asphyxiation or hemorrhage, and 3) perhaps achieve cure by early complete resection. Knowledge of the anatomy and physiology of the laryngotracheal complex is crucial in planning the appropriate resection. We present a case of locally advanced thyroid cancer (tall cell variant), invading the trachea, in a 54 year-old female. appropriate preoperative workup including CT/MR imaging and endoscopy help evaluate the feasibility and extent of resection. This video demonstrates the technical complexities and considerations involved in tracheal surgery. a precise knowledge of the regional anatomy along with meticulous dissection is essential to successful outcome. A total thyroidectomy with a sleeve resection of the trachea is performed. The surgical anatomy and procedure along with the postoperative management is outlined. Familiarity with the management of well differentiated thyroid cancer invading the trachea, including tracheal resection and reconstruction is necessary for surgeons involved in the care of patients with advanced thyroid cancer.