Airway management is a vital part of anesthesia practices, intensive care units, and emergency departments, and a proper pre-operative assessment can guide clinicians’ plans for securing an airway. Complex airway assessment has recently been at the forefront of anesthesia research, with a substantial increase in annual publications during the last 20 years. In this paper, we provide an extensive overview of the literature connected with pre-operative airway evaluation procedures, ranging from essential bedside physical examinations to advanced imaging techniques such as ultrasound (US), radiography, computed tomography (CT), and magnetic resonance imaging (MRI). We discuss transnasal endoscopy, virtual endoscopy, 3D reconstruction-based technologies, and artificial intelligence (AI) as emerging airway evaluation techniques. The management of distorted upper airways associated with head and neck pathology can be challenging due to the intricate anatomy. We present and discuss the role of recent technological advancements in recognizing difficult airways and assisting clinical decision making while highlighting current limitations and pinpointing future research directions.