Superior mesenteric artery syndrome (SMAS) is an uncommon condition which is difficult to diagnose due to non-specificity of symptoms. The most common causes of SMAS are severe weight loss secondary to severe medical conditions, surgical history, and cancer. A 31-year-old male with a history of ulcerative colitis status-post proctocolectomy with ileal pouch-anal anastomosis 10 years prior, presented with progressively worsening weight loss and abdominal pain. Radiographic imaging was consistent with SMAS, which was subsequently confirmed intraoperatively during an emergency surgery in which a Roux-En-Y gastrojejunostomy was performed. Clinicians should be aware that SMAS is a rare but possible complication of ileal pouch-anal anastomosis. Although rare, there should be a low threshold for this diagnosis when obstructive symptoms present.