This article outlines the historical and contemporary landscape of tobacco production and marketing in Zimbabwe. It highlights patterns of boom and bust dependent on global demand, trading frameworks and degrees of government support to the industry, which are reminiscent of cycles of tobacco production elsewhere in the region. It illustrates at the national and farm level the importance of diversified marketing channels: how the Zimbabwean tobacco industry has twice been at the intersection of two distinctly different global tobacco markets and has, with varying degrees of success, managed to survive and thrive by balancing the competing demands of buyers in these different domains. At the farm level, peasants now also have diversified marketing channels and are able to select between the auction floors and a range of contracting companies. The article outlines a case study of contracting practices in Mashonaland East and highlights that there is currently a lack of functional organisational platforms that can help to redress power imbalances between peasants and contracting companies. It concludes by outlining an incremental approach to setting a regulatory framework that can set sufficient checks and balances for producer associations to hold contracting companies to account.