Reconstruction of the maxilla following cancer resection has evolved over the past decade. Underpinned by advances in virtual surgery technology and an increased focus on dental rehabilitation, more sophisticated workflows using free bone flaps have become more commonplace. There are few reconstructions anywhere in the body that require the restoration of similarly intricate bone and soft-tissue relations with implications for both form and function, like the maxilla. Success demands careful anatomical definition of the defect, an understanding of the goals and principles of reconstruction, and the understanding of relative strengths and limitations of the various reconstructive options. Equally, as no one technique is without shortcomings and maxillary surgery can be associated with a significant complication profile, it is just as important to match the patient and oncologic context to the reconstruction. This article is intended to provide the reader with a broad overview of these core factors.