Central America was one of the principal regions where transnational peasant organizing emerged and from which it spread in the late 1980s and early 1990s. Yet by the late 1990s the seemingly powerful transnational peasant coalitions were in disarray. Their successors have had only a modest impact since 2001. The article points to two main sources of weakness in Central America's transnational peasant coalitions: first, a variety of intra-organizational problems, including political differences, disputes over resources, over-funding by cooperation agencies, and an emphasis on networking activity, rather than concrete gains, as a measure of success; and second, an external political, economic and demographic environment that has become increasingly unfavourable. Elements of the latter include the long-term declines in maize and coffee prices, only recently reversed in 2006; the declining importance of agriculture and the imposition of a new economic model centred around industrial and financial activities; and the rapidly growing levels of out-migration and of dependence of those remaining in the countryside on family remittances and non-agricultural activities. The article concludes not with definitive arguments, but rather with a series of questions about what might constitute effective strategies for transnational peasant organizing in an extremely problematic context, such as contemporary Central America.