The most common primary non-epithelial neoplasms of the gastrointestinal (GI) tract are gastrointestinal stromal tumors (GISTs). Ten percent (10%) of GISTs arise from the jejunum. Usually, patients complain of abdominal discomfort, but they may present with complications such as intestinal obstruction or bleeding. This report describes a 35-year-old male who presented with unusually massive, acute lower GI bleeding. After resuscitation and investigations (including a contrast-enhanced computed tomography of the abdomen and lower GI endoscopy), the patient underwent diagnostic laparoscopy and bowel resection of the affected section with anastomosis, and he had an eventful postoperative course. Studies suggest that GI bleeding in GIST occurs due to the ulceration and necrosis of the overlying mucosa caused by the pressure effect of the mass. Small-bowel GISTs are categorized based on their size. Many guidelines have advocated conservative management for small GISTs (<2 cm) that are in the jejunum. This patient has a rare case of a small jejunal GIST with a rare presentation of massive lower GI bleeding. A multidisciplinary approach is useful in managing such cases, and our case showed that laparoscopic intervention is a feasible option in a stable patient with massive lower GI bleeding.