When tracheal invasion of cancerous diseases such as thyroid cancer occurs, tracheal resection followed by end-to-end anastomosis is a treatment of choice. Anesthetic management of the patient during this procedure may pose challenges, such as maintaining ventilation during tracheal dissection, resection of the tracheal invasion, and tracheal end-to-end anastomosis. Here, we have presented a case of a woman in her 50s. Computed tomography of the head and neck displayed a 31-mm mass in the medial lobe of the thyroid gland, and irregularities in the trachea and right tracheoesophageal groove. We decided to perform total thyroidectomy followed by tracheal resection and end-to-end tracheal anastomosis, as a radical treatment. Anesthetic management was successfully performed without a decrease in the peripheral blood oxygen saturation level, due to managing oxygenation by using the oxygen reserve index (ORI TM ) monitoring during the tracheostomy, tracheal infiltration division resection, and tracheal end-to-end suturing. This case was a unique situation requiring two intraoperative tube exchanges, but the ORI monitoring of oxygenation enabled safe anesthetic management.