A visual search assistance system and related operating method are disclosed. An exemplary embodiment of the method dynamically determines a desired line-of-sight vector from an occupant of a vehicle to a visual target, and dynamically determines, with an onboard tracking system of the vehicle, an actual line-of-sight vector for the occupant of the vehicle. The actual line-of-sight vector is temporally associated with the desired line-of-sight vector. The method compares the actual line-of-sight vector against the desired line-of-sight vector to obtain a difference measurement, and generates a notification when the obtained difference measurement exceeds a threshold value. The notification provides guidance to redirect a gaze direction of the occupant toward the visual target.