Surgical education has seen immense change recently. Increased demand for iterative evaluation of trainees from medical school to independent practice has led to the generation of an overwhelming amount of data related to an individual’s competency. Artificial intelligence has been proposed as a solution to automate and standardize the ability of stakeholders to assess the technical and nontechnical abilities of a surgical trainee. In both the simulation and clinical environments, evidence supports the use of machine learning algorithms to both evaluate trainee skill and provide real-time and automated feedback, enabling a shortened learning curve for many key procedural skills and ensuring patient safety.