A 92-year-old patient with surgically altered anatomy (total gastrectomy with Roux-en-Y for gastric cancer) presented with recurrent biliary obstruction. Imaging revealed gallbladder and common bile duct (CBD) lithiasis. The patient was unfit for surgery, prompting an endoscopic approach. i) First, EUS-guided transjejunal gallbladder drainage was performed using a 10×10-mm LAMS with coaxial pigtail plastic stent. ii) Four weeks later, antegrade trans-LAMS access to the CBD was unsuccessful. A second EUS-guided biliary drainage (choledochojejunostomy) was created with a 6×8-mm LAMS, followed by transpapillary dilation and double-pigtail stent placement (10 Fr × 7 cm). This case demonstrates the feasibility of sequential EUS-guided biliary drainage for complex biliopancreatic disease in altered anatomy.