System, methods, and other embodiments described herein relate to improving vigilance and readiness of an operator in a vehicle that includes an augmented reality (AR) display. In one embodiment, a method includes computing an engagement level of the operator to characterize an extent of vigilance decrement and readiness presently exhibited by the operator relative to operating characteristics of the vehicle including an external environment around the vehicle and at least semi-autonomous operation of the vehicle. The method includes dynamically rendering, on the AR display, graphical elements by varying visual characteristics of the at least one graphical element as a function of the engagement level and based, at least in part, on sensor data about the external environment. Dynamically rendering the at least one graphical element improves the at least semi-autonomous operation of the vehicle through inducing vigilance and readiness within the operator with respect to the operating characteristics.