We describe the case of a patient with the rare complication of a chronic postaural fistula following repeated and extensive surgery and adjuvant radiotherapy to the head and neck for a pleomorphic adenoma of the parotid gland. This case demonstrates the importance and value of thorough preoperative planning for major head and neck reconstruction, particularly if the area for reconstruction has distorted anatomy due to prior treatment or damage. In complex free flap reconstruction, it is important to investigate the recipient site with the help of arteriography and give due consideration to the donor site and its postoperative management. We highlight the importance of multidisciplinary work for the care of these patients not only intraoperatively, but also in the preoperative planning stage, and perhaps most importantly in the postoperative care.