CASE PRESENTATION: A 52 year male presented with respiratory distress, left side chest pain, and fever for six days. All these symptoms proceeded by 5 episodes of vomiting. A chest x-ray done by some other physician, which revealed left side pleural effusion about 300 ml fluid was aspirated, but there was no improvement in symptoms. At this time we received patient in our hospital. Patient was dyspnoeic with a respiratory rate of 38 breaths/min, pulse of 114 beats/min, and blood pressure of 130/74 mmHg. Clubbing, cyanosis, lymphadenopathy, or subcutaneous emphysema were absent. Chest examination revealed findings suggestive of left hydropneumothorax. A provisional diagnosis of left hydropneumothorax (iatrogenic) was made. Initial investigations haemoglobin of 10.8 mg/dL, total leucocyte count 14,600/mm3 with 75% neutrophils. Serum electrolytes, blood urea, liver function test and electrocardiogram were with in normal limits. chest x-ray showed a left sided hydropneumothorax. The patient was put on oxygen, and broad-spectrum antibiotics. A contrast enhanced computed tomography (CECT) scan and barium swallow was done. CECT showed a left sided hydropneumothorax and pneumomediastinum. Barium study showed a leakage of contrast to the mediastinum. Patient was immediately shifted to Cardio Thoracic Surgery for operative intervention.