Cystic artery pseudoaneurysms (CAP) are rare and occur as a result of chronic inflammatory conditions or trauma including a difficult laparoscopic cholecystectomy. We present a case of a 66-year-old female who presented to our emergency room with a two-day history of abdominal pain, jaundice, and melena, symptoms which were retrospectively identified as components of Quincke's triad. After an initial endoscopic retrograde cholangiopancreatography (ERCP), the patient underwent an attempted laparoscopic cholecystectomy complicated by massive bleeding requiring conversion to attempted open cholecystectomy, and damage control surgery. After angioembolization of the cystic artery, the patient returned to the operating room and cholecystectomy was performed. This case highlights this rare presentation where unplanned initial management can result in life-threatening consequences.