A 59-year-old female with a history of achalasia, thoracoscopic longitudinal myotomy (35 years prior), laparoscopic Heller myotomy and Dor fundoplication with repair of hiatal hernia one year prior, and esophageal dilation for dysphagia one month prior, presented to the emergency department with hematemesis and left-sided chest pressure. Imaging with computed tomography of the chest with intravenous contrast showed a focal area of active extravasation within the distal esophagus (Figure A). Esophagogastroduodenoscopy revealed blood in the lower third of the esophagus with a large red clot obstructing the lumen (Figure B).