Esophagopleural fistula (EPF) is a rare complication often associated with underlying esophageal malignancies. We present the case of a 64-year-old male who presented with left-sided pyopneumothorax and was diagnosed with EPF secondary to esophageal carcinoma. Imaging studies revealed a hydropneumothorax with an esophageal-pulmonary fistula communicating with the pleural cavity. The diagnosis was confirmed through computed tomography (CT) scan with oral contrast administration, highlighting the utility of this modality in diagnosing EPF. The patient was further referred to the surgical oncology team for esophageal resection and fistula closure.