The brutal nine-year conflict in Sierra Leone has defied both military solutions adopted by various governments and peace accords imposed by the international community and regional powers. The latest casualty is the controversial Lomé Accord, which gave power and amnesty to the rebels in a power-sharing government. This article offers explanations for the failures by focusing on the interplay between the policy choices of decision-makers and the country's governance institutions and social structure. The policies of decision-makers can have negative consequences on societies if they are grounded on institutions that are at variance with a country's social structure. The article develops three main arguments to support this conclusion. First, the country's bipolar ethnic structure and majoritarian presidential system of government act as serious constraints on policies that seek to forge a national coalition to end the war. Second, conventional armies in ethnically polarised settings are a poor instrument for fighting rebel groups that deliberately use mass abductions and terror as war strategies. Third, peacemakers do not understand the institutional contexts in which violence-prone rebel groups can be made to reclaim their humanity and observe peace agreements. The logic of the interconnections between territory, resources and civilisation suggests that Sierra Leone's rebels are unlikely to accept disarmament and honour the democratic road to peace.