Black esophagus or AEN syndrome is an important cause of upper gastrointestinal hemorrhage with striking endoscopic presentation in a clinically compromised individual with multiple co-morbidities. Structured conservative management with correction of underlying etiology and acid suppression is essential to improved prognosis. Associated duodenal pathology on endoscopy is a reflection of the degree of initial insult and a clinical predictor for potential stricture development. Proximal extension of the black esophagus may be related to the degree of hyperglycemia. Increased awareness of AEN syndrome will lead to early recognition and proper treatment.