Gallstone ileus is an uncommon occurrence and accounts for about 0.3–0.5% of complications of cholelithiasis in elderly patients. Bouveret syndrome is an uncommon medical condition resulting from the blockage of the duodenal bulb by a stone, which consequently obstructs the outlet of the stomach. Until now, a comparison of two different presentations of Bouveret syndrome has not been published in the literature due to the rarity of this pathology. The curious simultaneous occurrence of the two cases discussed here made it possible for us to compare the different diagnostic and therapeutic pathways. In fact, both cases differ not only in their presenting symptoms, but also in the management adopted by the same surgical team.