This chapter focuses on the history and role of key technological advances in craniofacial surgery. With the advent of new tools, our abilities to perform complex procedures continue to evolve. Novel approaches to the neonate with syndromic craniosynostosis that combine strip craniectomy and posterior vault distraction are only feasible with virtual surgical planning (VSP). Augmented reality (AR) and robotic approaches to complex head and neck syndromes hold potential in improving future critical evaluation and understanding of complex cranial morphology. With the increasing spread of artificial intelligence (AI) throughout all technological applications, the analysis of clinical problems and outcomes will likely catalyze our surgical abilities and techniques. This chapter will analyze the historical context, applications, advantages, and limitations of VSP, AR, robotics in craniofacial surgery, and AI in relation to craniofacial surgery and, particularly, Apert syndrome.