This chapter provides an analysis of the cyber insurance landscape and begins with an overview of the cyber insurance ecosystem, presenting the cyber insurance life cycle and the main and secondary actors. It examines organisational decision-making involving cybersecurity and cyber insurance, both for companies as a whole and for Small and Medium Enterprises in particular. The chapter presents the cyber insurance ecosystem and discusses the different types of actors involved in the ecosystem and the relationships between them. Companies must make key investment decisions concerning cybersecurity measures on a regular basis, but there is a lack of research directly investigating how companies make these decisions, as identified by Weishaupl et al. There are many different processes influencing cybersecurity-related decisions inside a company. There are also many different factors, both internal and external, that can influence companies' cybersecurity decision-making and cyber insurance adoption. Many of impediments to cyber insurance adoption are problems that arise when companies try to buy cyber insurance.