The osteomyocutaneous iliac crest free flap is a reconstructive option for segmental mandibular or complex palatomaxillary defects. Familiarity with the radiographic appearance of free flaps such as the iliac crest is necessary for the postoperative evaluation of patients after mandibular, maxillary, or palatal reconstructions because it allows radiologists to properly monitor and interpret the appearance of the flap over time. This study presents a retrospective review of 5 patients who underwent palatomaxillary reconstruction with an iliac crest free flap at our institution. The imaging appearances of the 5 patients were analyzed to determine the key radiographic characteristics of a healthy and successful iliac crest free flap. Radiographic fluency with the imaging appearance of the iliac crest free flap, as well as the new anatomy of the region in the postoperative period, will allow for better interpretation of the flap appearance on imaging and will prevent false identification of tumor recurrence.