The purpose of this chapter is to examine current data related to anesthetic management for oncology patients undergoing free flap reconstruction after surgical resection. Due to case complexity, radiotherapy history, patient comorbidities, and increased incidence of difficult airway, head and neck reconstruction surgeries often pose numerous challenges to the anesthesia care team. Anesthesia and surgery for head and neck reconstruction often result in a shared airway situation. It is paramount to have clear communication among all perioperative team members and establish a preplanned strategy for airway management. Significant tobacco and alcohol use, environmental exposures, and transmission of human papillomavirus are significant risk factors for the development of head and neck cancers. Of these cancers, the vast majority present as squamous cell carcinomas. Underlying comorbid cardiovascular and pulmonary disease, postradiation fibrosis, electrolyte abnormalities, and dehydration are commonplace in this patient population. Case management must include a proper approach to advanced airway management and optimization of patient condition while maintaining ideal conditions for successful free flap reconstruction.