Spontaneous oesophagus rupture, also known as Boerhaave syndrome, is a rare but near-fatal medical condition and despite recent medical advancements, it remains a diagnostic challenge for front-door clinicians. The authors describe a similar presentation in an elderly gentleman who presented to the emergency department with sudden chest pain post vomiting. His initial chest radiograph showed bilateral dense consolidations and pleural effusions, and was treated as sepsis secondary to bilateral pneumonia. He underwent computed tomography pulmonary angiogram to rule out pulmonary embolism because of his chest pain with elevated D-dimer which confirmed the diagnosis of oesophagus rupture. His care was transferred to Surgical and Intensive care colleagues with plans for radiological chest drain insertion to limit contamination of mediastinum, however the patient became hypoxic and hypotensive and despite maximal organ support passed away within 6 hours of admission. Retrospect review of chest radiograph revealed Peri-oesophageal air tracking, a sign of Boerhaave syndrome. The aim of this case is to emphasise the importance of raising the suspicion of Boerhaave syndrome in patients with sudden chest pain, unexplained pleural effusion or pneumothorax with a history of recent vomiting as early diagnosis holds the key to prompt lifesaving management.