Superior mesenteric artery syndrome is characterised by vascular compression of the third part of the duodenum, resulting in obstructive symptoms. This case has been selected for its unusual presentation with pneumomediastinum and for the strikingly abnormal cross-sectional findings. We present the case of a young male of asthenic build, who was admitted to hospital with a history mimicking Boerhaave's syndrome (spontaneous oesophageal perforation). Radiological features included pneumomediastinum, but also an astonishing degree of gastric and duodenal dilatation. Extraluminal retroperitoneal air was also noted, further complicating the patient's presentation. We explore the relevant imaging and surgical findings, and relate these to an initially puzzling diagnostic dilemma.