Gastrointestinal stromal tumors (GISTs) are the most common mesenchymal tumors of the gastrointestinal tract. GISTs of the small bowel are rare, and often present with an abdominal mass and/or bleeding. Chemotherapy and surgery are the mainstay of therapy. Here, we discuss an unusual case of a ruptured jejunal GIST with hemoperitoneum and recurrence despite surgical excision followed by Imatinib treatment. Forty-five cases of ruptured small intestinal GISTs were identified in the literature. Most cases were in males and were found to be at the site of the jejunum.