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This paper investigates two fundamental questions related to safety and insurance in the age of automation. First, we touch upon the question of safety and liability under infrastructure-assisted automated driving. In such an environment, automakers provide vehicle automation technology while infrastructure support service providers (ISSPs) provide smart infrastructure services. Additionally, customers can receive coverage for accidents from either of these actors but also from legacy auto insurers. We investigate the effect of market structure on safety and accident coverage and show that an integrated monopoly provides full coverage and fully accounts for accident costs when choosing safety levels. However, in the Nash setting, even though full coverage obtains, lack of coordination leads to partial internalization of accident costs by the automaker. Moreover, multiple equilibria might exist, some of them undesirable. We show that, both in the presence and absence of legacy insurance, an appropriate liability rule can induce optimal safety levels under the Nash setting. Our second question concerns itself with the role and welfare effects of the availability of legacy auto insurance in the age of infrastructure-assisted automated driving. Our analysis shows that the industry is not necessary for optimal coverage when the cost of accidents is known in advance and all possible accident scenarios are contractible. In fact, their presence can even harm safety, even though it ensures full coverage for accidents. When only insurance contracts with capped liability for automakers and ISSPs are available and in a monopolistic environment, legacy insurance potentially harms welfare. This highlights the important role of market structure in assessing the future of insurance in the age of automated driving and lays the groundwork for future investigations in this direction. • Accidents will not disappear in an automated driving market. • Multiple actors in this market: automakers, smart infrastructure operators, and legacy insurers. • How should liability and insurance be apportioned in this context? Is there still a role to play for legacy insurers? • We design and analyze a welfare-maximizing rule for liability sharing. • We show the importance of market structure in determining whether and how legacy insurance will affect welfare in the future. [ABSTRACT FROM AUTHOR]