During the past century tobacco production and marketing in Nyasaland/Malawi has undergone periods of dynamism similar to changes since the early 1990s. This article highlights three recurrent patterns. First, estate owners have fostered or constrained peasant/smallholder production dependent on complementarities or competition with estates. Second, the rapid expansion of peasant/smallholder production has led to large multiplier effects in tobacco-rich districts. Third, such expansion has also led to re-regulation of the marketing of peasant/smallholder tobacco by the (colonial) state. The article concludes by assessing whether recent changes in the industry – such as district markets, contract farming with smallholders, and the importance of credence factors – have historical precedents, or are new developments in the industry.