The drive for making colonial territories “profitable” through various means, such as commodity extraction, got entangled with complex events that stood well beyond the intervening capacity of colonial administrators, and labour migration was no exception. This article analyses Makonde migration from Northern Mozambique toward sisal plantations in neighbouring British Tanganyika during the twentieth century and argues that the interweaving of written and oral sources renders two contrasting pictures: one of an orderly planned commodity sector mediated by industrial pundits and sustained by a rhetoric of colonial “development”; and another of spontaneous, haphazard yet rational life decisions undertaken by migrant men and women. We challenge the conventional take on African labour migration by discussing a much more complex picture that shows how the colonial labour migration system had to address the migrants’ needs and how migrants successfully subverted coercive structures for their benefit, and by doing so, Makonde migrants established their own transformative connections with global phenomena that outreached their participation in commodity production chains