Transforming intersections into roundabouts has shown that a sufficient degree of road safety and traffic capacity can be achieved. Because of the lower speeds at the area of a roundabout, drivers tend to become more easily adaptive to any kind of conflict with the surrounding environment. Despite the contribution to safety, the design elements of roundabouts are not uniformly fixed on a worldwide scale because of different traffic volumes, vehicle dimensions, drivers’ attitude, etc. The present study provides a brief overview of the contribution of roundabouts to road safety and the interactions between safety and the design elements of roundabouts. In addition, discussion points about current challenges and prospects are elaborated, including findings from the environmental assessment of roundabouts; their use and performance on the era of autonomous vehicles that will dominate in the near future; as well as the role and importance of simulation studies towards the improvement of the design and operation of roundabouts in favor of safer vehicle movement. The criticality of roundabouts, in terms of their geometric design as well as the provided road safety, lies upon the fact that roundabouts are currently used for the conventional vehicle fleet, which will be gradually replaced by new vehicle technologies. Such an action will directly impact the criteria for road network design and/or redesign, thereby continuously fostering new research initiatives.