Esophagopleural fistula (EPF) is rare despite the anatomical proximity of the esophagus and the pleural space. A 64-year-old man presented with a pneumothorax after a fall requiring chest tube placement. An esophagogastroduodenoscopy revealed severe LA grade D esophagitis and a large EPF in the distal esophagus. Computed tomography scan revealed that subtle tracking of air extending from the distal esophagus into the right pleural space was noted. The patient was treated with placement of a fully covered esophageal metal stent, and he recovered uneventfully. Interpreting key subtle clues in pleural fluid analysis and imaging can lead to a timely diagnosis and thus improves morbidity and mortality of EPF.