Background. Bouveret syndrome and gallstone coleus are two rare subsets of gallstone ileus. Bouveret syndrome involves a gastric outlet obstruction, whereas gallstone coleus involves an obstruction of the large intestine. Both of the conditions are caused by gallstones, which migrated from the gallbladder via the fistulae. Due to its rarity, only few cases were reported for each condition. The current case describes an even rarer case of Bouveret syndrome and gallstone coleus presenting together. The case report will hopefully provide better understanding of the disease presentation and hence, lead to early diagnosis and management. Case. Ms. B is an 86-year-old woman of Italian background who presented to our emergency department with worsening symptoms of bowel obstruction. Her past clinical history included Kaposi sarcoma, hypertension, osteoarthritis, and vitamin D deficiency with surgical history including caesarean section and tonsillectomy. On her imaging, she had two large gallstones, one in the proximal duodenum and one in the distal colon. It also showed gastric dilatation and gas in the gall bladder. She was subsequently diagnosed with Bouveret syndrome with concurrent gallstone coleus. The laparotomy revealed two points of gallstone obstruction at the first part of the duodenum and at the distal sigmoid colon. Her postoperative recovery was uncomplicated. She was discharged to the care of her family and followed up in the general surgery clinic. Conclusion. The current case report describes a unique presentation of Bouveret syndrome where an additional gallstone was found simultaneously in the sigmoid colon causing the obstruction. By introducing this novel case of having two different subsets of gallstone ileus simultaneously, there will be a better understanding of both conditions and hopefully improve our scope of practice.