Background: Acute esophageal rupture is a rare emergency that must be diagnosed quickly and treated aggressively to avoid significant morbidity and mortality. The typical presentation of this disease includes chest pain, and the diagnosis is challenging when cardinal features such as this are absent. Objectives: This case report discusses an atypical presentation of esophageal rupture in a patient with a predisposing condition and highlights the diagnostic and cognitive difficulties involved in making the appropriate diagnosis. Case Report: We report a case of a 51-year-old woman who presented to the Emergency Department with hypotension and an emergency medical services report of hematemesis. The patient had a documented history of upper gastrointestinal bleeding and Zollinger-Ellison syndrome during her past hospitalizations; however, the patient was not anemic and had a negative stool guiac despite symptoms for 3 days. A subsequent chest radiograph led to the diagnosis of esophageal rupture with a bilateral pneumothorax requiring thoracostomies. She reported no chest pain. Conclusions: The esophageal rupture and subsequent hypotension was likely secondary to the combination of her Zollinger-Ellison syndrome and recent vomiting episodes. It is important to avoid premature diagnostic closure and think about unusual presentations of emergent conditions such as esophageal rupture.