We report a case involving a 55-year-old man who had a recent resection of tracheal carcinoma and tracheal reanastomosis. He subsequently developed tracheomalacia and anastomotic dehiscence requiring airway stenting via an armored endotracheal tube (ETT). Placement of the armored ETT was technically difficult. It required insertion of an airway exchange catheter through the tracheal stoma to oxygenate, ventilate, and serve as a guide for ETT placement through the tracheotomy and across the dehiscence. During transtracheal jet ventilation our patient developed bilateral tension pneumothoraces requiring cardiopulmonary resuscitation and chest tube placement. The patient was quickly recovered, stabilized, and later discharged after a prolonged intensive care unit (ICU) course. We review the recommendations for jet ventilation via airway exchange catheters, common problems during this technique, and potential methods for avoiding these problems. The risk of barotrauma and pneumothoraces during jet ventilation via an airway exchange catheter should be kept in mind.