We report the case of a patient with pancreatic adenocarcinoma who underwent pancreatico-duodenectomy and later developed two malignant afferent-loop strictures causing biliary tract dilation and jaundice. An initial EUS-guided gastroenterostomy (EUS-GE) was created using a 15×10 mm LAMS placed between the stomach and the best visualized segment of the afferent loop, located between the strictures. Despite technical success, the patient developed cholangitis due to an unaddressed proximal stricture. The initial LAMS was secured with an X-Tack system to prevent migration. Through an endoscopic ultrasound-directed transgastric intervention (EDGI), a second 15×15 mm LAMS was deployed across the proximal stricture. This stepwise strategy achieved full symptom resolution and biochemical normalization. The case highlights effective combined use of EUS-GE and EDGI in post-surgical anatomy.