Subglottic tracheal stenosis can occur after prolonged intubation or tracheostomy. This stenosis can become severe and causes symptoms refractory to endoscopic interventions that require tracheal resection. This surgery presents unique anesthetic issues due to the airway anatomy, physiology, and shared airway management with the surgical team. We present the case of a 68-year-old patient who underwent cervical tracheal resection and reconstruction due to persistent symptoms despite balloon dilation and medical management with oxygen and heliox. Our anesthesia management involved several techniques that allowed the safe completion of this procedure. Firstly, we started the airway management with a combined size 4 Ambu® AuraStraight™ (Denmark) supraglottic airway device and flexible bronchoscopy to allow localization of the stenosis and dilation before endotracheal tube (ETT) placement. The conventional approach for this endoscopic evaluation phase is to use rigid bronchoscopy. Secondly, we used prior CT images to help guide our ETT tube size selection. Thirdly, we used total intravenous anesthesia during most of the procedure because of the intermittent apnea necessary to complete the tracheal resection. Lastly, extubation had to be done very carefully to minimize excessive patient neck movement and avoid any reintubation. Both could lead to a catastrophe with the newly reconstructed trachea.