Bouveret syndrome, a rare complication of cholelithiasis resulting in gallstone ileus, presents diagnostic and therapeutic challenges due to its low incidence and nonspecific symptoms. We report a case of Bouveret syndrome in a middle-aged male without significant medical history, emphasizing the need for heightened clinical suspicion. Diagnostic imaging, including computed tomography and upper endoscopy, revealed gastric outlet obstruction and a cholecystoduodenal fistula. Treatment involved unsuccessful endoscopic lithotripsy followed by surgical intervention. This case underscores the importance of interdisciplinary collaboration for successful management. With no standardized approach, individualized treatment strategies, including endoscopic and surgical interventions, are crucial for favorable outcomes in Bouveret syndrome.