This open access book offers a forward-looking analysis of how digital disruption and cross-border dynamics are reshaping insurance law. Further, it shares legal and regulatory insights into the challenges posed by new technologies and evolving market structures. The first section explores digital realities-from insurance in the metaverse and robo-advisers to blockchain-based duties and the role of copyright law in digital distribution. In turn, the second section discusses jurisdictional and cross-border issues, including barriers to life insurance passporting, fairness in group insurance, broker cooperation, and the influence of EU soft law on national markets. These topics are highly relevant, as they reflect the real-world pressures on legal systems to adapt to innovation while maintaining fairness, accountability, and coherence. The book addresses the regulatory and legal gaps emerging from this transformation, helping readers navigate the resulting complexities and uncertainties. Given its scope, it will be of interest to legal scholars, regulators, practitioners, and advanced students in the fields of insurance law, financial regulation, and digital governance.