An aircraft-based pilot safety system (PSS) includes cameras or other gaze sensors fixed at an aircraft pilot and configured to capture an image stream focused on the pilot's eyes. The gaze sensors continually assess the gaze direction of the pilot (e.g., toward a display, instrument panel, and/or indicator within the cockpit that the pilot is currently looking at or focusing on) and thereby can establish when the pilot is executing a scan pattern and if that scan pattern is nominal for the current flight context by comparing the scan pattern to context-specific reference scan patterns. If, for example, the pilot's gaze deviates from where it should be (e.g., as determined by the current flight segment) or the current scan pattern is interrupted, the system may prompt the pilot to redirect their gaze or resume the scan pattern.