Bouveret's syndrome is an unusual clinical presentation of gastric-outlet obstruction and is the most infrequent variant of gallstone ileus with just over 300 cases in the literature. A 73-year-old female presented with innocuous constitutional symptoms and was found to have Mirizzi type Vb, a cholecystoduodenal fistula with obstruction. Esophago-gastroduodenoscopy-attempted dislodgement was unsuccessful. A gastric-jejunal bypass was the only option due to friability of the tissue. On post-op day 5, the patient developed acute abdominal pain and was found to have gallstone ileus. This case emphasizes the importance of early surgical intervention in cases of acute on chronic cholecystitis.