Establishing political legitimacy is a concern of all political regimes and leads to a range of legitimating techniques to suit particular circumstances and regime objectives. For Bhutan, the challenge has been how to legitimate a new democratic political order that did not result from citizen or elite pressure, the normal causes of democratic transition. This article addresses how legitimacy has been secured in Bhutan, a nation of “reluctant democrats”. It uses a methodology derived from an amalgam of longue durée and critical junctures to analyse the country’s unique process of democratisation, as some of the building blocks of contemporary democratic legitimation have old origins. By dividing Bhutanese history into four distinct periods and identifying four critical junctures, this article provides a full understanding of the nature and process of contemporary democratic legitimation. We pay special attention to the role of the monarchy in facilitating and securing acceptance of the new political order and in guaranteeing the monarchy’s future as a central pillar of that order. An important lesson of this article is the need to take a historical perspective when considering contemporary legitimacy as history reveals the building blocks on which today’s democratic regime legitimacy has been built and accepted.