The rehabilitation of maxillectomy defects can be initiated at the time of resection through interactive treatment planning between the surgeon and maxillofacial prosthodontist. The purpose of this article is to familiarize the recent generations of head and neck surgeons and maxillofacial prosthodontists with the role of the surgical obturator and intraoperative techniques for optimal prosthesis design. The advantages of a surgical obturator and the consequences of not using a surgical obturator for maxillary resections are evaluated. Different types of defects are assessed from the initial presentation to completed design of cast and surgical obturator. The surgical and prosthetic techniques to aid fabrication of surgical obturators for three subjects with very different maxillary defects are shown. Emphasis is placed on the value and versatile functionality of a surgical obturator to initiate and promote successful rehabilitation of the maxillary defect.