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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. The EU AI Act introduces horizontal rules governing AI systems, including those used in automated underwriting, risk profiling, and robo-advisory services, thereby directly affecting the design and accountability of algorithmic tools in insurance distribution, especially those deemed high-risk. The DSA imposes new responsibilities on digital platforms, with potential implications for InsurTech firms acting as intermediaries or aggregators. Additionally, there is ongoing uncertainty as to whether existing consumer protection instrument, such as the Unfair Contract Terms Directive (93/13/EEC), the Unfair Commercial Practices Directive (2005/29/EC), and the Omnibus Directive (2019/2161/EC), are sufficient to address the novel risks and challenges posed by digital insurance services. Meanwhile, regulatory guidance from supervisory bodies such as EIOPA and national authorities is increasingly addressing InsurTech-related legal questions in a more targeted manner. 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.