Abstract Introduction Biliary leaks are a frequent complication of hepatobiliary surgery. We present a particularly complex case. Clinical case A 46-year-old man underwent S4-8 hepatic bisegmentectomy for hepatocellular carcinoma. Two months later he underwent percutaneous drainage of a liver collection and later endoscopic placement of plastic biliary stents. Due to the persistence of the leak, it was decided to intervene surgically by suturing the biliary leak, draining the main bile duct using a Kehr drain, and cholecystectomy, with apparent resolution. Two months later, sudden dyspnea with yellow-green emission, persistent cough, and episodes of bile vomiting appeared. CT of the chest and abdomen confirmed the presence of a biliobronchial fistula and a subdiaphragmatic biloma connected to the hemidiaphragm and initial parenchymal irritation. Percutaneous drainage of the biliary collection and thoracotomy surgery (transdiaphragmatic repair of biliary fistula, atypical lung resection of the right lower lobe, pleural cleaning, and diaphragmatic plastic surgery) were performed. One month later, with the subdiaphragmatic collection persisting, a Roux-en-Y biliojejunal anastomosis, transjejunal loop, and liver drainage (U tube) were performed, along with drainage of the interhepatodiaphragmatic collection. Subsequently, one month later, due to the persistence of the bile leak with interhepatodiaphragmatic collection, another Roux-en-Y anastomosis of the parenchymal fistula in the residual cavity was performed. After 14 days, the patient was discharged in good clinical condition, which lasted over time, without collections. Discussion This case illustrates the complexity that can be associated with a common complication of hepatobiliary surgery.