Despite its many benefits, there are several potentially significant complications inherent to chest tube insertion (CTI), a commonly used invasive procedure to evacuate air or fluid from the pleural space. The average rate of complications following CTI ranges from 5% to 10%, whereas insertion‑related complications are rare. Here, we present the case of a 45‑year‑old female suffering from a motor vehicle accident who developed Grade IV liver laceration complicated with intra‑abdominal hemorrhage and right‑sided fractures from the fourth to the ninth rib. Misplacement of the preventive CTI for potential hemopneumothorax during the first attempt was observed by computed tomography and simultaneously led to diaphragmatic penetration. Subsequently, massive bloody pleural effusion from the abdominal cavity through the defect in the right hemidiaphragm was noted through a newly inserted chest tube when the patient coughed due to endotracheal suctioning. This case illustrates the significance of identification of patients at high risk for complications related to CTI and the utility of ultrasound guidance during CTI.