Injury to the common bile duct (CBD) during upper gastrointestinal surgery for peptic ulcer disease is a serious complication with an underestimated prevalence in light of the few cases reported in the surgical literature. Three cases of CBD injury were referred to a multidisciplinary specialized gastrointestinal unit for management over a 4-year period. Anomalous anatomy, adhesions, and potential duodenal shortening secondary to contracture all predispose the biliary ducts to intraoperative injury. The axial nature of the blood supply to the extrahepatic ducts and the tendency of bile itself to cause rapid collagen turnover and fibrosis, combined with the inflammation and subsequent fibrosis to the surrounding tissues caused by bile leakage, give the bile ducts a high propensity for stricture formation. Frequently presenting symptoms of CBD injury immediately after surgery include jaundice, elevated bilirubin values, elevated t-tube drainage, and symptoms of sepsis. The most common complaints noted in patients who present in a delayed manner are symptoms of cholangitis. Even when injuries are rapidly identified and corrected, the potential for lasting negative impact on quality of life is great in many cases. When CBD injury occurs, the pancreatic duodenal union can be concomitantly disrupted.