A 72-year-old female underwent pylorus-preserving pancreaticoduodenectomy due to a non-ampullary HDG LST of the descending duodenum (R0). Post-surgical adverse events included a millimetric jejunal perforation due to the migration of the surgical pancreatic stent against the limb wall. During the endoscopic retrograde treatment attempt of the perforation, a dehiscence of the hepaticojejunostomy was noticed and addressed by placing an enteral fc-SEMS and through-the-meshes biliary fc-SEMS. Subsequent EUS-guided antegrade fc-SEMS was placed through the pancreaticojejunostomy to guarantee an access route to retrieve the migrated pancreatic surgical stent. Challenges with stent migration led to further interventions, highlighting the complexities of postoperative management following pancreatic surgery and the pivotal therapeutic role of a multimodal endoscopic approach.