This edited volume examines how recent technological innovations are transforming European insurance law, focusing on critical issues such as transparency, information duties, fairness, and the regulation of insurance contracts for both professional and private policyholders. While new business models, like digital platforms and robo-advisory services, are rapidly emerging, European law has yet to provide a sufficiently tailored regulatory response. The current sectoral framework, notably Directive (EU) 2016/97 on insurance distribution (IDD), offers a general, principle-based approach, but lacks the specificity needed to effectively address innovative digital insurance distribution models. In parallel, broader regulatory initiatives such as the EU Artificial Intelligence Act (EU AI Act) and the Digital Services Act (DSA) are poised to reshape the digital insurance ecosystem. By providing a normative and comparative legal analysis, this volume addresses a significant gap in current scholarship. It calls on legal scholars and insurance experts to reassess the role of technology in shaping EU insurance law and to reflect on whether the regulatory principle of technological neutrality remains viable. Ultimately, the book argues for an integrated regulatory approach that aligns socio-technical governance with the specific demands of insurance law, ensuring effective consumer protection in an increasingly digital landscape.