Small bowel gastrointestinal stromal tumor (GIST) is an uncommon tumor, with an estimated frequency of 10-20/L million population, occurring usually in the 6 th decade of life. GISTs, mainly ones larger than 4 cm have a wide range of presentations from abdominal discomfort and bloating to abdominal emergencies due to massive gastrointestinal (GI) hemorrhage, with pressure necrosis and ulceration of the overlying mucosa is the main mechanism leading to GI hemorrhage. Life-threatening hemorrhage is a rare initial presentation. Among the wide differential diagnosis for GI bleeding, jejunal GIST is one of the rarest etiologies. Due to its location and hence the inability to identify by endoscopy it is difficult to diagnose. From here, computed tomography (CT) angiography is considered essential for identification of the site of GI bleed, which aids in diagnosis of GIST. The mainstay treatment for this emergent presentation is resection, which if done in a timely manner results in a good clinical outcome. Herein, we report a case of a 46-yearold male patient presenting with massive GI bleed from jejunal GIST, leading to hemodynamic instability, requiring massive transfusion protocol managed by small bowel resection, after failure of radiologic embolization. In rare instances GISTs present as massive GI bleeding necessitating admission to the hospital and urgent interference. In our case the early multidisciplinary approach manifested by involvement of interventional radiology with the surgical team was the cornerstone in the successful management of our patient and should be considered in all cases of massive upper GI bleeding.