Pulmonary complications of rib fractures typically occur in the immediate postinjury period, as a result of the forces causing the injury or subsequent rib fracture displacement. Pneumothorax, hemothorax, pulmonary contusions, or parenchymal lacerations are frequently seen with significant chest wall trauma. Hemopneumothorax is typically treated with tube thoracostomy, and full resolution of the pleural injury is expected; continued pleural fluid accumulation despite these measures is unanticipated, rare, and quite problematic. We report a case of hemorrhagic pleural effusion after rib fractures that were recurrent despite several tube thoracostomies and computed tomography-guided aspirations. The patient subsequently underwent operative fixation of her rib fractures, with successful resolution of her symptomatic pleural effusion.