Accurate diagnosis and characterization of maxillofacial pathology require imaging techniques that extend beyond purely morphological assessment to capture tissue composition, vascularity, and physiological behavior. The maxillofacial region presents unique diagnostic challenges due to its complex anatomy, close proximity of diverse tissue types, and frequent overlap in imaging appearances of inflammatory, benign, and malignant conditions. Advances in contrast-enhanced imaging have substantially strengthened diagnostic performance across computed tomography, magnetic resonance imaging, and ultrasonography by improving tissue differentiation, lesion conspicuity, and assessment of disease extent. Unlike conventional non-enhanced imaging, modern contrast-based approaches enable integrated evaluation of structural, functional, and biological characteristics of lesions. This chapter provides a comprehensive overview of the principles, mechanisms, and clinical relevance of contrast enhancement in maxillofacial imaging. It examines endogenous and exogenous contrast mechanisms in CT, including contemporary developments in contrast expression and quantitative assessment, advances in MRI contrast behavior and biological classification of contrast agents, and the evolving role of contrast-enhanced ultrasonography in real-time soft tissue and vascular evaluation. Emphasis is placed on how contrast enhancement refines lesion characterization, supports differential diagnosis, and improves clinical confidence in complex maxillofacial conditions. By synthesizing physical principles with clinical application, this chapter highlights the expanding role of contrast-enhanced imaging as a cornerstone of modern, precision-oriented maxillofacial radiology.