A system and method for continuous real-time assessment of the situational awareness of an aircraft operator incorporates gaze sensors to determine the current gaze target (or sequence of gaze targets) of the operator, e.g., which interfaces the operator is looking at. The system receives operational context from aircraft systems indicative of current events and conditions both internal and external to the aircraft (e.g., operational status, mission or flight plan objectives, weather conditions). Based on the determined gaze targets and coterminous operational context, the system evaluates the situational awareness of the operator relative to the operational context, e.g., perceptive of the operational context; comprehending the operational context and its implications, and projecting the operator's perception and comprehension into responsive action and second-order ramifications according to task models indicative of expected behavior.