Background: The majority of small bowel obstructions (SBOs) that require operations are caused by adhesions after previous operations, hernias, and cancer. Undigested foods of the appropriate size are an unusual source of endoluminal SBOs. Methods: Case report and review of the literature. An 83-year-old female with a history of dementia was admitted with increasing abdominal pain and tenderness. A computed tomography (CT) scan demonstrated a SBO with a small bowel mass at the transition point in the distal ileum. Urgent laparotomy revealed a closed loop SBO requiring an ileocectomy. Results: Analysis of the specimen revealed an undigested grape and multiple raisins. Conclusions: Phytobezoars are an unusual source of life-threatening SBO. Risk factors include poor dentition and dementia. The diagnosis can be made using careful history taking, physical exam, and appropriate imaging, preferably a CT scan. At risk patients should be counseled on appropriate dietary measures to prevent this dangerous condition.