Cholelithiasis is a common gastrointestinal pathology that can lead to rare complications including cholecystoduodenal fistulas and GI hemorrhage. Diagnosing cholelithiasis and cholecystoduodenal fistulas in the emergency department (ED) using computed tomography (CT) imaging despite nonspecific and variable symptoms is critical in determining management strategies for medically complex patients. An 87-year-old medically complex female presented to the ED in hemorrhagic shock after several episodes of hematemesis, hematochezia, and other nonspecific gastrointestinal symptoms. A CT of the abdomen/pelvis was performed revealing cholecystitis with a large 6-cm stone; additionally, a biliary enteric fistula was noted with blood products in the gallbladder. This case highlights the importance of CT imaging in the setting of gastrointestinal bleeding with cholelithiasis and biliary enteric fistula diagnosis, and discusses potential management strategies of these diagnoses in medically complex patients