Regulating AI means addressing issues that could harm public trust in AI systems and the organizations (public and private) using them. Financial Services firms are prolific users of, investors in and insurers of AI and Emerging Tech, such as algorithmic social scoring, and biometric identification. As key pillars of functioning economies and society-at-large, the responsibility for Financial Services firms is to be not just operating within the rule of Law but operating to the highest Cultural standards—especially where the rule of Law is lacking, inadequate or a work-in-progress (as is the case with AI). This is a matter not just for the firm but for systemic stability, globally. This chapter explains the concept of Cultural Intelligence (CQ), and how it can be applied to ethical issues around AI in the organisation; and using these ideas as context and a reference point, presents a snapshot view of the experience and views of UK Insurance (owned by or owning EU firms, embedded in supply chains, servicing customers globally, and facing legislative and regulatory developments well beyond the UK and EU Insurers offer an excellent window into the realities of digital commerce within a (sectoral) regulated context for Legal professionals.) Legal professionals, how they’re navigating the gaps between the rule of law and the realities of AI in the firm today, and what developing the firm’s ability to ‘do’ CQ for AI could look like. A ‘How’s our ability to ‘do’ Culture (CQ)?’ lens is applied inwards, to the firm’s own internal communities of functions and experts and societal stakeholders, drawing out key themes from the Insurance’s sector experience with (Personal) Data, automated profiling (social scoring) and decisioning. An analysis of UK Consumer Duty is offered as both an example of failed CQ, and an opportunity to ensure that Insurance firms do a better job of navigating similar gaps between the ‘rule of Law’ and what’s happening on the ground in the firm now, for AI in Financial Services.