A number of options exist for patients with anticipated difficult intubation on account of a retrosternal goiter compressing on the trachea. The chosen technique(s) to secure the airway in this delicate situation often depends on the location and degree of airway obstruction, available resources/facilities, and an anesthetist's experience and preferences. We report the case of a 68-year-old woman with severe airway obstruction from a retrosternal goiter coming for total thyroidectomy. Airway management started with an awake fiber-optic intubation, proceeded to a tracheostomy and finally to use of a rigid bronchoscope following failure of the earlier techniques to achieve adequate ventilation.