This paper reports the diagnosis and management of two elderly male patients with recurrent pneumothorax who developed the rare complication of chest tube misplacement into lung tissue after insertion of a 24-Fr chest tube. Both patients presented with poor drainage and subcutaneous emphysema following tube placement, and the diagnosis was confirmed by chest computed tomography (CT). As conservative management, we adopted a strategy of reinserting a new chest tube at an alternative site to promote lung re-expansion. Both patients were discharged uneventfully, with good lung re-expansion observed during follow-up. These cases suggest that for elderly patients with recurrent pneumothorax and those at high risk of pleural adhesions who require chest tube drainage, preoperative chest CT evaluation, selection of an appropriate insertion site, digital exploration of the pleural cavity during the procedure, and avoidance of chest tubes with an introducer stylet are crucial for preventing this complication. When chest tube misplacement into the lung tissue occurs, leaving the original tube in place to provide a partial tamponade effect while simultaneously inserting a new chest tube may serve as a safe and effective first-line conservative strategy.