Gastrointestinal stromal tumours (GIST) are rare gastrointestinal tumours and are one of the causes of obscure gastrointestinal bleeding. We report a case of massive gastrointestinal bleeding secondary to bleeding jejunal GIST in a 43 years old gentleman. Endoscopic intervention failed to identify the source of bleeding and CT Angiography (CTA) showed a jejunal mass and patient underwent laparotomy and resection of the bleeding jejunal GIST. This article highlights the rare cause of the massive GI bleeding and also emphasise the role of CTA in obscure GI bleeding.