This chapter aims to describe the thematic connection between supervisory actions and multidimensional consumer perceptions of insurance services and contracting in the age of digitalization. The consumer perceptions studied here are based on earlier research while supervisory actions are drawn from practical examples identified through the Internet. The supervisor-consumer relationship can be seen as an illustrative case for the examination of wide interaction relationships where industry actors do not necessarily interact directly with each other. The chapter demonstrates that utilising an ecosystem approach offers a fruitful intellectual method for better understanding the dynamics, nature and development of the insurance industry. More generally, the insurance industry represents a truly interesting context to study ecosystems at the intersection of public and private sectors and organisations.