Toll plaza designs have implemented electronic toll collection and other technologies to improve toll systems; however, an increase in crashes has appeared with these improvements. To study safely the pertinent aspects of driver behavior in toll plazas with electronic toll collection, a cockpit driving simulator housed at the University of Puerto Rico at Mayagüez was used. Specifically, in this study a comparison was made of two configurations of the signs that indicated the corresponding speed limit and toll station for each lane in the area before the toll plaza. One configuration corresponded to the current condition of the signage in Puerto Rico, with signs located at the roadside; the second configuration presented a proposed overhead signage treatment. A representative group of 20 subjects was selected to test the effectiveness of the two signage configurations on the approach zone leading to the toll plaza, calculating the standard deviation of roadway position, speed, and acceleration noise in five zones. The behavior of drivers using the proposed signage configuration appeared to be safer than the behavior of drivers following the current signage configuration. Specifically, at each of five zones in which behavior was sampled on the approach to the toll plaza, drivers using the proposed configuration changed lanes more smoothly and reduced their vehicles’ velocity more when approaching the toll plaza. Nevertheless, there was no significant difference between configurations in acceleration noise. The results of this study provide strong evidence that driving simulators can be used effectively to identify efficient and inexpensive alternative signage configurations at toll plazas.