In mineral-rich regions of Sierra Leone, the diversification of livelihood portfolios is widespread, and rural communities have long pursued complex and dynamic strategies that involve the intertwining of mining and farming activities. In recent years, however, alluvial diamond deposits in the Eastern District of Kono have increasingly become ‘worked out’, and artisanal mining communities have had to adapt and demonstrate resilience. Building on a rich body of field-based research that the authors have carried out over the past 20 years, this paper critically explores both the constraints and opportunities that are currently shaping youth resourcefulness and self-reliance, as well as the government's policy response to rapidly changing conditions in mining communities. It argues that although it remains the case that artisanal and small-scale mining (ASM) operations continue to dovetail with a wide range of other livelihood activities, they are fast becoming the alternative, as miners shift to other forms of livelihoods, including agriculture. This shift, the paper argues, is however not a smooth process, as miners making the transition are faced with a myriad of challenges including lack of access to finance and agricultural inputs. As a result, communities are ‘stuck’ in transition despite a renewed interest in farming driven by a parallel resurgence of associational life in rural areas. While the problem of youth marginalisation and unemployment in Kono have long received considerable attention from both the government and civil society, whether or not the evolving policy response is able to keep up with the current rapid pace of change in artisanal mining communities remains open to question.