Malpositioning is one of the most common complications of chest tube insertion and is associated with increased morbidity and mortality. We present two cases of patients with chronic obstructive pulmonary disorder (COPD) in whom malpositioned chest tubes penetrated through the anterior mediastinum to the contralateral pleural cavity, and were later removed without complications. Both patients had a relatively wide retrosternal airspace and received blunt dissection with a trocar for percutaneous chest tube insertion, which may have increased the risk of chest tube penetration through the anterior mediastinum during tube thoracostomy. Further, the precise location of the malpositioned chest tubes could not be confirmed by single-view anteroposterior portable chest radiography, and computed tomography (CT)-scan was more helpful in the diagnosis and management of the cases reported herein.