Bouveret's syndrome is a rare complication of cholelithiasis, characterized by gastric outlet obstruction caused by a migrated gallstone. Diagnosis of Bouveret's syndrome necessitates urgent treatment as it carries a high mortality rate. The treatment of Bouveret's syndrome has traditionally been surgical. However, there have been increasing reports of successful endoscopic therapy for Bouveret's syndrome. This case series aims to compare and contrast two cases of Bouveret's syndrome. The gallstone was retrieved via endoscopic access in one case while the other was removed with surgery. For each case, we discuss the various factors that contributed to the decision of which treatment modality to use. In addition, we propose an endoscopic technique that may improve the safety and success rate of endoscopic treatment of Bouveret's syndrome.