The chapter focuses on innovation and law, not merely on digitalization and law. The reason for this broader focus is simple: Digitalization is an innovation. Furthermore, digitalization is an innovation that has already for some decades been, and still is today, a great challenge not only to insurance contract law, but to the entire insurance law, the entire contract law, the entire private law, and the entire legal system. However, it is not the first innovation that the law, and insurance law in particular, had to face. Legal history and insurance legal history have seen countless innovations of different types. In the present contribution, I wish to discuss, by way of example, two such innovations, to analyse their effects on insurance law and the law in general, and to reflect on what these lessons from history may teach us for the general theme of the present volume: “European Insurance Law within the Digital Age”. Thus, the present chapter focuses, in essence, on the questions of how the law and lawyers have reacted in the past to innovations and what we can learn from history how to approach today the many challenges that digitalization poses.