We present five cases of pylorus-preserving pancreaticoduodenectomy (PPPD) after endoscopic ultrasonography-guided choledochoduodenostomy (EUS-CD) using a lumen-apposing metal stent (LAMS) as a bridge to surgery in patients with resectable distal malignant biliary obstruction and failed endoscopic retrograde cholangiopancreatography (ERCP). The patients underwent an EUS-CD using EC-LAMS, the bile duct being accessed using the transbulbar approach. The technical success rate of EUS-CD was 100%. No procedure-related adverse events occurred. All patients underwent PPPD with a technical success rate of 100%. The presence of a transduodenal LAMS did not impede surgery. No biliary or duodenal fistula occurred in the patients. Pancreatic fistulas with late bleeding were observed in two patients (one fatal). These few cases indicate that PPPD after EUS-CD using LAMS is feasible and safe. EUS-CD should be performed irrespective of the stage of the disease, also for patients fit for surgery. Additional larger prospective studies are required to confirm this preliminary data, in particular for possible interference with postoperative outcomes.