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 four recurrent patterns. First, estate owners have either fostered or constrained peasant/smallholder production dependent on complementarities or competition with their estates. Second, rapid expansion of peasant/smallholder production has led to three recurrent outcomes: a large multiplier effect in tobacco-rich districts; re-regulation of the marketing of peasant/smallholder tobacco by the (colonial) state; and, lastly, concerns over the supply of food crops. The article concludes by arguing that whilst the reform of burley tobacco production and marketing in the 1990s engaged with the first two issues, it may have benefitted from paying greater attention to the latter two issues as well.