The Republic of Somaliland remains internationally unrecognised in spite of its declaration of independence in 1991, yet the people have achieved a degree of stability, indeed democracy, that is currently unthinkable in the southern and central areas of Somalia. Somaliland’s stability has been built on the back of overwhelming popular support for sustained peace, which in its turn has enabled a series of elections for different branches of government. While much has been made of the role played by customary Somali approaches to mediation and conflict resolution in enabling this development, we argue that an essential element in the application of this custom is its very pragmatism. ‘Tradition’ is invented and reinvented as negotiations take place and agreements are reached. It is this flexibility which has allowed Somalilanders thus far to negotiate the difficult task of accommodating the institutions of representative democracy where Somali custom prefers direct forms of (male) democracy. For some this represents a transition from ‘tradition’ to ‘modernity’, though we question the validity of such binary opposites, and see the transition as both incomplete and fragile. We argue that, while progress along a democratic path to date has been remarkable, it is incumbent on the international community to seek practical ways of furthering engagement with Somaliland, without imposing solutions, if that progress is to be maintained. We also consider a number of specific constitutional and political issues that we believe require attention if the gains made to date are to be consolidated.