Britain has long taken a firm public line against terrorist ransom, insisting that yielding to terrorist demands only encourages further acts of intimidation and kidnapping. Hitherto, academic research has tended to take these assertions of piety at face value. This article uses a historical approach to show that the British position has shifted over time and was often more complex and pragmatic. Indeed, Britain’s position with regard to kidnap and ransom insurance has, until quite recently, been rather ambiguous. We use the British case to suggest that, rather than dividing states into groups that make concessions and those that do not, it is perhaps better to recognise there is often a broad spectrum of positions, sometimes held by different parts of the same government, together with the private security companies that move in the shadows on their behalf. One of the few things that unites them is a tendency to dissemble and this presents some intriguing methods problems for researchers.