A 77-year-old male was presented to the emergency department with 24-h history of abdominal pain, nausea, vomiting, and constipation. Physical examination was unremarkable. Laboratory showed elevated total bilirubin, liver transaminases, and lipase. Abdominal CT demonstrated a complex density 5-cm duodenal mass and double-bubble appearance of the stomach divided by a stalk. MRCP (Image 1) demonstrated duodenal mass (blue arrow) with corresponding dilation of the common biliary duct (red arrow), gallbladder (yellow arrow), ampulla of Vater (green arrow), and pancreatic duct (white arrow). After initial management with IV fluid, patient’s symptoms were resolved. Upper endoscopy demonstrated large submucosal mass in gastric fundus, dilated pylorus, and normal duodenum. Diagnosis of gastro-intestinal stromal tumor (GIST) was made. GISTs are relatively uncommon tumors of the gastro-intestinal (GI) tract developing from interstitial cells of Cajal. They may present with GI bleeding or could cause intraluminal obstruction. Patient’s symptoms recurred the next day. He was taken into operative room. Laparoscopy (Image 2) demonstrated gastro-duodenal intussusception (white arrow) and mass in the duodenum (black arrow). Reduction of the intussuscepted tumor followed by wedge gastric resection was performed. Pathology confirmed GIST within free resection margins. The patient recovered promptly and remained asymptomatic on outpatient follow-up.