The chapter introduces Churchill’s army career between 1895 and 1900, but does so from an important new perspective: using his exploits in Cuba, India, the Sudan and South Africa to explore the origins of his lifelong interest in intelligence and clandestine operations. It argues that his first foray overseas to Cuba was in the ‘well-established tradition of the British amateur spy’ but that he maintained his interest in military intelligence thereafter through the connections he made to support his writing and journalism on the Indian north-west frontier, while attached to Kitchener’s expedition in the Sudan and later as a war correspondent and then soldier in South Africa. The author looks at the intelligence lessons that Churchill learned, including the power of guerrilla insurrection, the importance of properly resourced intelligence services, the comparative roles of the civil and military intelligence arms and the need for a managed relationship with the press.