Anterior mediastinal masses are challenging. As induction of general anesthesia may result in complete airway obstruction or hemodynamic collapse, maintaining spontaneous ventilation and advancing the endotracheal tube (ETT) distal to the mass are recommended. We discuss the emergency management of an anterior mediastinal mass-induced near-complete airway obstruction at the carina. Despite maintaining spontaneous ventilation, airway obstruction persisted following placement of the ETT proximal to the obstruction. After advancing the ETT into the right mainstem bronchus distal to the mass, hypoxemia persisted, prompting placement of a second ETT into the left mainstem bronchus to overcome the obstruction and provide adequate oxygenation.