Over the past two decades, protecting contractual parties reasonable expectations has incrementally gained judicial recognition in English contract law. In contrast, however, the similar doctrine of policyholders reasonable expectations has been largely rejected in English insurance law. This is injurious, firstly, to both the consumer and business policyholders reasonable expectations of coverage of particular risks, and, secondly, to consumer policyholders reasonable expectations of bonuses in with-profits life insurance. To remedy these problems, this book argues for an incremental but definite acceptance of the conception of policyholders reasonable expectations in English insurance law. It firstly discusses the homogeneity between insurance law and contract law, as well as the role of (reasonable) expectations and their relevance to the emerging duty of good faith in contract law. Secondly, following a review and re-characterisation of the American insurance law doctrine of reasonable expectations, the book addresses the conventional English objections to the reasonable expectations approach in insurance law. In passing, it also rethinks the approach to the protection of policyholders reasonable expectations of bonuses in with-profits life insurance through a revisit to the (in)famous case Equitable Life Assurance Society v Hyman [2000] UKHL 39, particularly to its relevant business and regulatory background.