This chapter presents a comparative analysis of the mobility systems in Germany and Japan, providing insights into how these systems might influence the implementation of vehicle automation. This comparison begins by exploring the historical evolution of transport in both countries, noting that both have long-established infrastructures shaped by unique geographical and historical contexts. Germany’s transport system, for instance, developed within a landlocked nation with extensive rail networks, while Japan’s transport was influenced by its island geography and mountainous terrain. The chapter then examines key dimensions of the current transport systems, including demography, settlement patterns, road transport governance, public transport infrastructure, and the automotive industry’s role. Comparative statistics are provided, illustrating the differences and similarities between Germany and Japan. The analysis highlights how these existing systems serve as both enablers and barriers to the integration of automated vehicles. The chapter concludes that the introduction of vehicle automation will not revolutionize these transport systems overnight but will gradually adapt to existing frameworks. The success of vehicle automation depends on the interplay between technological advances and established transport policies, regulations, and cultural norms. This chapter suggests that understanding the deep-rooted structures of transport systems in Germany and Japan can offer valuable insights into how vehicle automation might unfold in other regions with mature mobility markets. In conclusion, the chapter provides a holistic framework for analyzing the potential impacts of vehicle automation, stressing the importance of considering the existing transport system’s legacy and the multifaceted nature of mobility in Germany and Japan.