Paraguay has been the target of foreign capital since the end of Triple Alliance War (1864-1870) when the Law of Public Land Sales (1883-1885) was established. This law significantly altered the country’s agrarian structure by initiating the private property of land, which resulted in the creation of latifundios (large land holdings) and a class of landless peasants. Afterward, it was not until 1970s that Paraguay has begun to experience significant agrarian transformation, mainly, because of South American regional dynamics, which demonstrate that the agrarian question is not restricted by political boundaries. As of 2008, in a context of multiple converging crisis, territorial disputes between transnational agribusiness – namely regional corporations – and the Paraguayan peasantry intensify because of the increase in land prices in South America and legislation that impose limits on agricultural land investments throughout other countries the region. This paper seeks to discuss how regional dynamics – especially those involving Argentina, Brazil and Uruguay – are reflected on Paraguay’s agrarian question and result in further dispute between transnational as well as trans-Latin agribusiness and the country’s peasantry.