Tracheoesophageal fistulas (TEF) present a perioperative management challenge. A 62 year-old man with esophageal carcinoma presented with a large tracheoesophageal fistula extending most of the trachea. Previously, the patient had two overlapping esophageal and one tracheal stent placed, but he developed progressive tracheal disruption due to esophageal stent perforation near the level of the cricoid. This case describes the anesthetic management of tracheal stent placement for an expanding TEF. Management included a spontaneous breathing inhalation induction followed by ventilation through a supraglottic device-laryngeal mask airway (LMA). Finally, during rigid bronchoscopy, a combination of bag ventilation and jet ventilation was utilized.