This article explores the role played by Chamberlain, Minto and Hutton in shaping the organizational and command structure of the Canadian expeditionary force that deployed to South Africa. In 1899, the war raised not only the vital question about the kind of imperial war Canada ought to participate in, but also the form of that participation. As this article demonstrates, the British politician, the colonial administrator and the general saw the war as an opportunity to advance their specific agenda, strongly fuelled by imperialist sentiments. In doing so, the ideas that shaped their actions between July and October 1899 provided the base for a succession of seemingly unrelated decisions that had a substantial influence on Canada’s contribution and on the command arrangements in South Africa. The Canadian soldiers who sailed to South Africa were, for the first time, grouped in a national military formation commanded by a Canadian officer, setting a precedent for the country’s participation in future conflicts.