Boerhaave's syndrome is the rare and often fatal condition of spontaneous oesophageal rupture. When present with atypical symptoms, diagnosis is frequently late, which contributes to the high morbidity and mortality. The authors describe a unique case of a 50-year-old man presented with atypical Boerhaave's syndrome, in which the diagnosis was made several days following presentation by observing a large pleural effusion that had evolved rapidly on chest radiographs. He was managed without thoracotomy. Although survival has been reported with non-operative management of contained oesophageal perforations, to our knowledge, this is the rare case report of surviving Boerhaave's syndrome with free pleural rupture, without thoracotomy.