This clinical vignette presents a decompensating 59-year-old woman with fatigue, melena, altered mental status, and subsequent hematemesis. Learners must rapidly identify upper-GI bleeding, recognize signs of hepatic encephalopathy, and manage suspected variceal hemorrhage in the context of alcohol-related cirrhosis. With findings including asterixis, hepatomegaly, jaundice, anemia, thrombocytopenia, elevated INR, and hyperammonemia, the case emphasizes early airway protection, massive transfusion, and the administration of octreotide and ceftriaxone. Trainees are challenged to prioritize interventions, anticipate deterioration, and coordinate care with gastroenterology for endoscopic hemostasis. The vignette also highlights when and how to use AIMS65, MELD, and GBS scores to predict mortality and triage care appropriately. Core emergency medicine principles (resuscitate before you intubate, manage coagulopathy, and protect the airway) are stressed throughout. This case reinforces critical thinking, leadership under pressure, and a systematic approach to shock in the setting of GI bleeding and liver failure.