Jejunal gastrointestinal stromal tumors (GIST) are rare mesenchymal tumors of the gastrointestinal (GI) tract and a rare cause of massive GI bleeding. Due to this rarity and non-specific presentation, diagnosis and treatment may be difficult and often delayed. Urgent surgical intervention is crucial for controlling the source of bleeding and total tumor excision. Herein, we present the case of a 40-year-old male who presented to the emergency room (ER) with features of upper GI bleeding. He referred astheny and black stools, and was pale, sweaty, and tachycardic despite normal blood pressure. Rectal examination revealed melena, and laboratory findings revealed decreased hemoglobin (Hb) and elevated blood urea. Upper endoscopy was normal, and the Hb level dropped again to 6.9 g/dL; therefore, blood transfusion was required during ER observation. For further investigation, the patient underwent an angio-computed tomography scan, which revealed a lesion located in a jejunal loop as the probable bleeding source. Emergency exploratory laparotomy revealed a jejunal loop tumor. Segmental enterectomy containing the tumor was performed and the post-operative period was uneventful. The anatomopathological examination was compatible with low-risk GIST, and the multidisciplinary board agreed that surveillance was the best ongoing treatment. Due to the rarity of jejunal GIST as the cause of massive GI bleeding, diagnosis may be challenging, delaying prompt treatment with bleeding source control. In such cases, surgery may be both lifesaving and curative. Therefore, these tumors should not be forgotten when managing patients with occult GI bleeding with an atypical presentation to prevent delays in treatment and severe outcomes.