Teen drivers have the highest crash risk when they start driving independently, and improving risk anticipation skills can help reduce this risk. Training can help teens acquire these skills faster and improve their overall safety record. The objective of this study was to evaluate an updated training program (based on RAPT and ACCEL) by introducing a more diverse set of training scenarios and leveraging deployment platforms that were better suited to modern devices. A pilot evaluation study was conducted with six teen drivers with less than six months of licensure to assess the updated training program (Risk-ATTEND). Risk-ATTEND was found to improve hazard anticipation-related gaze behaviors in teen drivers while also reducing workload. The research will aid in improving the training program’s usability, and web-based training will make the training program more accessible on modern devices.