This chapter reviews imaging approaches for osseous pathology of the maxillofacial skeleton, including osteomyelitis, jaw tumors, osteoradionecrosis (ORN), and medication-related osteonecrosis of the jaw (MRONJ). It emphasizes the importance of comprehensive clinical evaluation combined with appropriate imaging modalities—such as panoramic radiography, cone beam computed tomography (CBCT), medical CT, MRI, and nuclear medicine studies—for accurate diagnosis and management. Pathophysiology, risk factors, and characteristic imaging features of each condition are discussed, along with the role of emerging technologies like artificial intelligence in image interpretation.