Imminent upper airway obstruction due to life-threatening tracheal stenosis of any cause is a challenging situation. We present a challenging case of total thyroidectomy for a malignant, invasive, and highly vascularized thyroid carcinoma that has invaded the surrounding tissues, including the sternum and mediastinum, resulting in compression of the trachea with indentation. The patient presented with a significant symptomatic tracheal stenosis, the narrowest area of that was 4 mm. Airway management in such cases presents a particular challenge to the anesthesiologists, especially considering that the option of tracheostomy is very difficult most of the time due to the highly swollen thyroid and distorted anatomy. A meticulous history of the patient's illness had been taken, and a comprehensive preoperative evaluation was conducted, including construction of a 3D model airway, virtual endoscopy, and transnasal tracheoscopy. On the day of the surgery, the airway was managed through spontaneous respiration using intravenous anesthesia and the high-flow nasal oxygen (STRIVE-Hi) technique. It was then secured with intubation using a straw endotracheal tube (Tritube®) with an internal diameter (ID) of 2.4 mm and an outer diameter of 4.4 mm with the help of a fiberscope and D-MAC blade of a video laryngoscope. At the end of the procedure, the airway was checked with a fiber optic scope, which showed an improvement in the narrowed area. This enabled us to replace the Tritube with an adult cuffed ETT of size 6.5 mm ID, and the patient was transferred intubated to the surgical ICU. Two days later, the patient's tracheal diameter was evaluated with the help of a fiberoptic scope and extubated successfully in the operating theater.