The importance of good relations with regulators has never been more important. Regulation is fast becoming the key concern of compliance teams throughout the insurance sector meaning that understanding the approach and motivating themes behind each regulator is paramount. This can be difficult, there is no one-size-fits-all model of a regulator. Even an analysis of the recently created Financial Conduct Authority (FCA) and Prudential Regulation Authority (PRA) shows a distinct difference in regulatory approach and priority. The task of understanding a regulator's central concerns becomes even more fraught when comparing regulators across multiple jurisdictions. On this assessment it becomes apparent that the key to successfully navigating a regulator is an understanding of the economic, political and cultural landscape in which it is operating. In this article Charley Taggart and I explore and expand on these themes to offer an insight into how to maintain good relations with insurance regulators across the globe.