A 27-year-old female with a history of Crohn’s disease and familial adenomatous polyposis (FAP) presented to the emergency department (ED) with severe abdominal pain after an endoscopic exam. Chest and abdominal radiographs revealed massive pneumoperitoneum and the patient underwent emergent exploratory surgery. Herein, we discuss the management and outcomes of this case. The importance of a thorough history and physical exam when evaluating for an acute abdomen and thus the development of a successful management plan is also underscored.