Abstract   This paper critically examines some of the main challenges associated with facilitating ‘good governance’ in small-scale diamond-mining communities, focusing on the experience of Sierra Leone. Two recent governance initiatives in the country's diamond sector are reviewed: the Kimberley Process Certification Scheme (KPCS) for rough diamonds and the Diamond Area Community Development Fund (DACDF). The analysis considers some of the broader lessons that have emerged, as Sierra Leone currently attempts to launch a third governance initiative—the Extractive Industries Transparency Initiative (EITI). It is argued that the introduction of complex monitoring processes represents a significant challenge for a country that is emerging from a long period of conflict and isolation, is suffering from serious shortages in human capacity, and where good governance, accountability and transparency will undoubtedly take considerable time to develop.