Hemorrhagic cholecystitis with subsequent gallbladder rupture and torrential bleeding is a very rare but life-threatening complication of acute biliary tract diseases. Its clinical presentation may be dubious and therefore Computed Tomography (CT) imaging plays a crucial role in a prompt and accurate diagnosis. We present a case of a 64 year-old male who was admitted to the emergency department with clinical findings of acute cholecystitis. During the following hours the patient became hemodynamically unstable and an emergency abdominal CT scan was performed. CT revealed massive hemoperitoneum containing free gallstones. In addition, active extravasation of iv contrast material inside the gallbladder lumen was demonstrated. Based on these findings hemorrhagic cholecystitis with gallbladder rupture was suspected and the patient underwent urgent laparotomy. We describe specific CT findings of this rare condition, thus emphasizing the role of imaging in facilitating urgent surgical treatment.