An elderly gentleman presented with acute dyspnoea and right-sided pleuritic chest pain. Two-weeks previously an oesophageal stent had been inserted for dysphagia secondary to oesophageal carcinoma. With low PaO(2), a neutrophilic leucocytosis, raised inflammatory markers and a right-sided pleural effusion, antibiotics were prescribed for pneumonia. Computed tomographic pulmonary angiogram (CTPA) ruled out pulmonary embolus. The patient rallied transiently and his effusion improved. His respiratory distress returned 14 days later. A chest x-ray revealed a right-sided hydropneumothorax, and a chest drain-released stomach contents from the pleural cavity. A gastrografin swallow and endoscopy demonstrated malignant oesophageal rupture. An attempt to re-stent failed, and the patient returned to the ward for palliation. His initial presentation was likely that of an oesophageal leak, and not pneumonia. Oesophageal rupture is difficult to diagnose due to ambiguous signs, symptoms and radiological findings. Swift diagnosis significantly improves the outcome, therefore clinicians presented with similar cases should consider the diagnosis early.