Primary intratracheal masses causing luminal obstruction are relatively rare, posing a challenge for anaesthesiologists in airway management. This case report describes a distinctive airway management approach in a 71-year-old female patient with an aorta-carotid artery bypass graft that significantly obstructed the trachea. The patient presented with worsening shortness of breath, and a thoracic computed tomography scan revealed a 19.2 mm×9.9 mm×19.3 contrast-enhancing mass penetrating the right anterolateral tracheal wall, resulting in 80% occlusion of the tracheal lumen. Awake fiberoptic bronchoscopy (FOB)-guided nasotracheal intubation was performed following topical upper airway anaesthesia, with the patient positioned at a 30º head-up angle and slight right-up tilt to minimize discomfort. A 6.0 mm ID cuffed endotracheal tube was successfully placed under fiberoptic guidance distal to the intratracheal vascular graft but proximal to the carina. Intratracheal masses can lead to severe tracheal obstruction followed by progressive airway obstruction, which can be life-threatening when effective ventilation cannot be established after the induction of general anaesthesia. We recommend the use of awake FOB-guided intubation in such cases. Additionally, contingency plans should be prepared and meticulously prepared in the event of intubation or ventilation failure.