Currently, cities are in the midst of a transportation transition, namely, from human-driven to driverless vehicles. Because of the rapid development of technology, many systems are being automated or even becoming autonomous. Autonomous means that the system is able to perform each task automatically without any human intervention. Much research has been conducted to find answers to the way autonomous vehicles might impact cities. However, the results of this research are limited in practical application, because the integration of autonomous systems is still in an early stage and there have not been many integration projects in the world yet. In the Netherlands, more and more pilot projects are being established to explore the impact and applicability of driverless vehicles. As such, this exploratory study analyses how autonomous vehicles have been integrated during the autonomous vehicle transition in the Netherlands. Alongside qualitative research methods including desk research and semi-structured interviews, an analysis framework is designed and used as a means to measure the technical, social, environmental, and regulatory challenges represented in five case studies. The results show that the main challenges are, among others, road obstacles, intersections, weather implications, communication between the shuttle and other traffic flows, communication between the project team and the inhabitants of the area, and restrictions from the Dutch Vehicle Authority. Challenges such as weather implications, road obstacles, and intersections occur in each project. Looking at the current technological developments, there are autonomous vehicles that can pass intersections and obstacles already. The inability to deal with these challenges could be explained by the high costs of the technology.