Persistent or prolonged air leak (PAL) is one of the common complications that may happen after many procedures in thoracic surgery. The treatment may change based on the cause, and accordingly, the understanding and awareness of the causes and the exclusion of the rare causes are very important in the treatment of this condition. Here, we present an unusual case with PAL due to chest drain malposition with intraparenchymal insertion in an elderly patient who presented initially with a secondary spontaneous pneumothorax (SSP).