Undiagnosed tracheo-esophageal fistula remains an incredibly rare event in the anesthetized patient. We report the case of a 59 year-old female with a history of esophageal cancer requiring a stent who presented for posterior thoracic spine decompression and stabilization after a pathologic T2 vertebral fracture. Preoperatively, she complained of a chronic cough that she attributed to chronic gastroesophageal reflux and dysphagia. Shortly after induction of anesthesia and an unremarkable endotracheal intubation, the patient`s mouth was noted to foam oral secretions. Despite appropriate confirmation of adequate endotracheal tube position and cuff seal, concern for a tracheo-esopageal fistula emerged. Her endotracheal tube was repositioned distally beyond the suspected fistula. Bronchoscopy by thoracic surgery at the case conclusion confirmed the presence of a tracheo-esophageal fistula which subsequently failed to demonstrate clinically significant aspiration beyond the stent during a barium swallow evaluation. The case report helps to highlight the rare occurence of undiagnosed tracheoesophageal fistulae that can occur in patients with pre-existing tracheoesophageal pathology. The role of positive pressure in unmasking the latent fistula alongside the esophageal stent serves as a unique aspect for the case reported here. Available and relevant literature on stent-associated tracheoesophageal fistulae is reviewed in addition to concepts for management of newly diagnosed fistulae.