Gallstone ileus results in a mechanical small bowel obstruction when an itinerant gallstone tumbles downstream and obstructs the bowel lumen. Associated proximal intestinal injury with perforation is rare, and concomitant perforation of multiple segments of bowel in the setting of gallstone ileus has never been reported in the literature. We are reporting the case of a 67-year-old female patient who had gallstone ileus causing perforation of multiple segments of small bowel. At operation, she was found to have a 3.2-cm gallstone lodged at the terminal ileum, perforation of both the mid ileum and mid jejunum, and gross enteric spillage. She underwent removal of the gallstone and small bowel resection × 2. She was initially left in discontinuity with an open abdomen. She returned to the operating room 2 days later for bowel anastomosis and abdominal closure. She recovered well after surgery and was discharged home.