Complete or partial obstruction of the duodenum by the superior mesenteric artery (SMA) is a rare cause of bowel obstruction. SMA syndrome results from the compression of the 3rd part of the duodenum between the superior mesenteric artery and the abdominal aorta. Causes include anatomical variation in the superior mesenteric artery, trauma, burns, surgeries, malignancy, and rapid weight loss. Diagnosis of SMA syndrome in patients may be difficult, as the clinical findings often resemble other forms of small bowel obstructions. This syndrome was first described in the literature by Carl Freiherr von Rokitansky in 1861. Subsequently, David Wilke provided a comprehensive description of the disease in a series of 75 patients. There has been skepticism about the existence of SMA syndrome due to scant literature reports and non-specific symptomatology. However, modern cross-sectional imaging has confirmed the existence of this rare syndrome. Here we present the case of a 50-year-old female with longstanding symptoms of gastrointestinal discomfort, weight loss, nausea, and vomiting. She underwent an exhaustive gastrointestinal workup until a diagnosis of SMA syndrome was made. We elected to proceed with a minimally invasive three-port laparoscopic, trans-mesenteric side-to-side duodenojejunostomy. The patient was discharged on postoperative day one after tolerating a regular diet. On one month follow-up, our patient reported improvement in symptoms with no postprandial pain or nausea and normal bowel movements. In conclusion, we report a case of superior mesenteric artery syndrome in a patient with recurrent abdominal pain and nausea. CT scan has the highest sensitivity for the diagnosis of SMA syndrome, findings suggestive of the diagnosis include an abnormal aortomesenteric angle and distance. While supplemental tube feeds and gastric drainage may resolve the condition without the need for surgery, this often takes many weeks to months to be effective. Minimally invasive surgical bypass is an attractive option because of the rapidity of symptom resolution, lack of need for long-term invasive tubes, short inpatient length of stay, and high success rate.