Case Presentation: A 48-year-old Caucasian man with history of alcohol abuse, type II diabetes mellitus, hypertension, and multiple abdominal surgeries (partial gastrectomy, partial pancreatectomy, splenectomy and partial left nephrectomy) was transferred to our center for management of melena and shortness of breath. A computed tomography report from outside hospital (OSH) suggested dense material in the stomach and a left lung cavitary lesion, but images were not available for our review. Bronchoscopy revealed remnants of digested food in the left bronchial tree, which was attributed to aspiration at OSH. Soon after arrival to our facility, the patient developed an episode of large hematemesis requiring emergent intubation. GI was consulted for EGD, which did not suggest any gastric cause of bleeding, but a fistulous tract was recognized. Urgent repeat bronchoscopy revealed complete occlusion of the left main bronchus with a visible blood clots and food material. An arteriogram identified the source of the bleeding to be the left pulmonary and bronchial artery, but embolization was not successful and patient was taken for a thoracotomy and lung resection. Intra-operatively, a large abscess was found in the left pleural space with a communicating fistula to the stomach through a diaphragmatic defect. The fistula, gastric wall, and diaphragmatic defect were all successfully repaired and patient recovered well. Discussion: Gastropleural fistula is a rare but potentially lethal condition, which may occur as a complication involving one of three different mechanisms: perforation of the stomach (intrathoracic portion of hiatal hernia), traumatic event to the stomach or lung, or an intraperitoneal gastric perforation with erosion of a subphrenic abscess via the diaphragm. The cause of gastropleural fistula in our case is unclear. One possibility is aspiration pneumonia complicating into abscess, which eroded through the diaphragm into the stomach. Alternate etiology could be gastric in origin, whereby an ulcer eroded through an already adhesed area of a postsurgical stomach into the left lower lobe of the lung. It is important for gastroenterologists and endoscopists to remain cognizant about prior surgical histories, while managing patients with gastrointestinal hemorrhage because many of them may present with complications like gastropleural fistulae decades later.Figure 1Figure 2Figure 3