Intrapancreatic enteric duplication cysts are exceedingly rare, and the clinical presentation varies. We present a 48-year-old man with significant alcohol and tobacco abuse and a diagnosis of groove pancreatitis complicated by a pancreatic duct stricture, pseudocyst, and recurrent biliary obstruction. Due to failure of endoscopic therapy and concerning findings on endoscopic ultrasound with negative pathology, he underwent a pancreaticoduodenectomy. Pathology revealed an intrapancreatic enteric duplication cyst, minimal chronic pancreatitis changes associated with pancreaticobiliary strictures, and no evidence of malignancy. This rare diagnosis should be considered in the differential for patients with idiopathic recurrent pancreaticobiliary duct strictures and pancreatic pseudomasses.