This is a 12-year-old male with past medical history significant for nutcracker phenomenon of the left renal vein and a right inguinal hernia repair who presents with acute on chronic abdominal pain for 2 years. Patient reported severe epigastrium and right upper quadrant pain as well as multiple episodes of bilious and non-bilious emesis resulting in decreased oral intake and significant weight loss. Due to his extensive weight loss, the patient was placed on nasojejunal feeds as well as total parenteral nutrition. A CT abdomen/pelvis demonstrated possible SMA syndrome as well as compression of the left renal vein. He was taken to the operating room for a laparoscopic duodenojejunostomy, bypassing the portion of intestinal compression by creating an opening through the mesocolon. Post-operatively, the patient was able to return to oral feedings and successfully gained weight.