For successful organ transplantation patients are required to be on lifelong immunosuppression. These patients living in high ultraviolet radiation environments are more susceptible to skin cancers. When presenting with advanced skin cancers in the head and neck region they require specialist tertiary care. We present our experience of major head and neck surgery in transplant patients at an institution based separate to a transplant hospital. Over the last 12 months at the Royal Brisbane and Women’s Hospital we noted 130 patients undergoing major head and neck cancer surgery of which 30 patients were transplant patients. Of these 29 were male patients and 1 female patient with a mean age of 67. The most common pathology was squamous cell cancer and median staging was T3 disease. From our cohort 21 patients required major reconstruction in the form of a free flap. Of note 11 patients had already undergone radiotherapy. Transplant recipients have considerable medical, psychological and pharmacological changes therefore a clear understanding of the immunosuppressive drugs and the underlying surgical conditions is essential for these patients to undergo anaesthesia and surgery. Key clinical considerations require a coordinated approach in the preoperative period. Surgeons must remember to prioritise haematological considerations, medication levels and be mindful of cortisol/steroid management.