Reconstruction after circumferential pharyngolaryngectomy is a challenging problem. Reconstruction methods should ensure an appropriate mucosa lining of the digestive tract, preferably already tubulized, and peristalsis. Despite the high reported success rates, the jejunum flap is still occasionally lost due to thrombosis of the pedicle and/or fistula formation. Five cases of circumferential pharyngolaryngectomy in which failure of the jejunum loop was managed with a second free or pedicle flap are presented. A second free jejunum was reliable in selected patients, depending on time of detection of flap necrosis, on bacterial control of the wound and on the vascular or general conditions. For this reason, careful monitoring of the flap and clinical signs of necrosis in the first 5 post-operative days is crucial to prevent the formation of fistulas and infection and to increase the possibility of using this kind of salvage surgery. Pedicle flaps should be used only in the event of severe complications because of their high risk of post-operative salivary fistulas.