A gravida 6, para 4 mother presents with spontaneous labor at 37 1/7 weeks’ estimated gestational age (EGA). The pregnancy is uncomplicated, but ultrasonography reports polyhydramnios. Delivery occurs via repeat cesarean section. Copious oral secretions and significant work of breathing are noted at delivery, requiring positive pressure ventilation and intubation of the newborn. The patient undergoes extubation a few days after birth and is weaned to room air. Oral feeds are attempted after extubation, but choking and gagging occur. The care team discusses possible differential diagnoses, such as esophageal atresia/tracheoesophageal fistula (TEF), esophageal webs, esophageal strictures, esophageal diverticulum, tubular esophageal duplications, congenital short esophagus, and tracheal agenesis/atresia. During an upper gastrointestinal series, the patient has bradycardia and desaturations. The study images are interpreted as an H-type TEF. A gastrostomy tube is placed to decompress the stomach, and nutrition is provided via total parenteral nutrition (TPN). The patient is also found to have a horseshoe kidney and an atrial septal defect. Microarray of chromosomes is normal. The patient continues to require numerous modes of ventilatory support including high-flow nasal cannula and reintubation. Because of a lack of improvement in respiratory status despite providing standard care for a TEF, the team investigates the patient’s anatomy more thoroughly. Bronchoscopy shows a large defect that connects the esophagus and larynx. The first attempt at tracheoplasty/esophagoplasty is performed via a lateral thoracotomy approach, but is ultimately unsuccessful. The patient returns to the operating room (OR), where a breakdown of the repair site and a blind pouch are noted on bronchoscopy between the carina and native esophagus. After this procedure, the patient is transferred …