The World Bank emphasizes land reform as a key pro-poor intervention, expecting the transfer of land to the rural poor to trigger a straight transition from poverty and subsistence to entrepreneurial and commercial smallholder farming. This article asks how and why World Bank prescriptions change in response to developments on the ground that contradict initial expectations, to show that the transition to commercialization is hardly a straight one, as it involves contradictory elements. It builds on an analysis of close to twenty years of World Bank reports on land reform in four post-communist countries to show how and why the transfer of land and commercialization end up contradicting rather than mutually supporting each other. The analysis shows that as a result of this contradiction, WB-inspired policies prioritize commercialization over poverty reduction, and their underlying understanding of poverty has changed from poverty as lack of farmland to poverty as lack of alternatives to farming. For the World Bank the problem in these countries is not so much the failure of having pro-poor results, but the decreasing control over smallholders, perceived to have responded to “insufficient” reforms by withdrawing from “markets” into “subsistence”. Yet the analysis further suggests that even though presently seen as a sign of underdevelopment, the “subsistence” capacity of local populations following land transfers was in earlier reports encouraged as it was believed to have the effect of supporting the commercialization of the sector and relieving welfare systems. This aspect of reforms is now relatively rarely mentioned and “subsistence” is assumed to be an effect of anything but reforms, cast instead as a sign of insufficient market creation.