A tracheoesophageal fistula (TEF), albeit rare, can be a life-threatening condition that requires prompt identification and treatment. Pulmonary contamination and restriction of proper nutrition are common, unfortunate consequences of untreated TEFs and are often the causes of mortality in this population. In our patient, a history of laryngeal malignancy along with symptoms of chest pain and cough with ingestion of liquids, even without evidence of aspiration pneumonia, appropriately prompted investigation for potential TEF. Initial imaging through barium swallow identified the TEF, and the patient underwent treatment with endoclips by endoscopy with bronchoscopic assistance.