Hepaticojejunostomy anastomotic stricture is a relatively uncommon postoperative complication after a Whipple procedure. However, they are increasingly being observed because of advancements in operative mortality rates and the widening of operative indications to include benign diseases such as chronic pancreatitis and intraductal papillary mucinous neoplasm. In this article, we describe a patient diagnosed with intraductal papillary mucinous neoplasm and another with pancreatic cancer, both of whom developed jaundice after undergoing the Whipple procedure. Subsequent investigation revealed a benign hepaticojejunostomy anastomotic stricture, successfully treated with stricturoplasty using a needle knife.