The authors report two cases of pharyngoesophageal reconstruction using free jejunum transfer, which required additional microsurgical reconstruction, due to total or partial loss of the free jejunal graft, despite successful microvascular anastomoses. Replacement and additional transfer of the second free jejunum segment were successfully carried out, with minimal risk and low morbidity. The second free jejunal transfer is one of the reliable reconstructive choices in the management of complicated pharyngoesophageal reconstruction with free jejunum.