A man in his 30s presented with a brief episode of vomiting, acute abdominal pain and subsequent development of shortness of breath. On initial examination and investigation, the clinical impression was of a right-sided pneumothorax, pneumonia and pleural effusion. Early antibiotic treatment and management showed a clinical improvement, with the patient reporting resolution of his symptoms. This episode was short lived, with a further deterioration in his condition and worsening of symptoms. Ensuing examination, imaging and investigations demonstrated an oesophageal leak into the right pleural cavity. Following urgent stabilisation measures and insertion of a chest drain, he underwent successful surgical repair. Boerhaave's syndrome is an emergency situation, requiring quick recognition, diagnosis, aggressive treatment and management to optimise a good outcome.