Two patients with underlying COPD and bullous changes of the lungs were found to have a loculated hemopneumothorax within a major fissure by computed tomography. Both patients had associated pleural disease. In one of the patients, the hemopneumothorax was believed to be potentially compromising pulmonary function. Percutaneous needle drainage of the loculated hemopneumothoraces resulted in large symptomatic pneumothoraces requiring urgent insertion of closed thoracostomy tubes. Loculated hemopneumothorax is an unusual finding within a major fissure mimicking pulmonary abscess, infected bullae, pulmonary cyst, or a cavitary carcinoma of the lung. Physicians treating patients with COPD and associated pleural disease should be aware of this rare condition, since percutaneous needle drainage may be associated with serious life-threatening complications.