Spontaneous transmural oesophageal perforation (Boerhaave syndrome) is a rare surgical emergency, the diagnosis and management of which has challenged clinicians for over 300 years. Even with best available modern management, it portends significant morbidity and a mortality rate of up to 60%. First described by Herman Boerhaave in 1724 to afflict the Grand Admiral of Holland, it was identified at that time only on autopsy, and Boerhaave opined gravely that it “cannot be remedied by any assistance of the medical profession”. It was not until 1914 that Irving Walker was the first to correctly identify spontaneous oesophageal perforation in a living patient, and although this did not alter the patient’s fatal outcome, it represented a change in mindset from the bleak one of Boerhaave, which ultimately led to the first operative cure in 1947. A flurry of case reports followed over the ensuing decades, detailing not only surgical repair of the oesophageal defect, but also management via oesophagectomy, and even occasional reports of survival with conservative management. Endoscopic management, first by stenting of the oesophagus across the defect, was described from the 1990s. As it stands today, several strategies for managing Boerhaave syndrome exist, including minimally-invasive surgical repair and endoscopic methods. Adjunct techniques, including early enteral feeding with jejunostomy tube placement, and mechanisms to divert oral and gastric secretions away from the healing perforation site, have also served to improve outcomes. While Boerhaave syndrome is no longer inevitably fatal, it remains a sobering presentation which tests even the experienced general surgeon.