With the war in Afganistan still going strong, there is a considerable interest in the military profession for insight into counterinsurgency war. This article argues that the five Southern African counterinsurgency wars – the Anglo-Boer War (1899-1902), the Portuguese colonial wars (1960-1974), the Rhodesian War (1965-1980), the Border War in Namibia (1968-1989) and the South African war against the ANC/SACP are valid illustrations of some of the rules being analysed in military literature nowadays. Mainly three lessons come out very strongly. One is the fact that counterinsurgency warfare is not about destroying an enemy army on the battlefield, but a struggle for the hearts and minds of the local population. The other is the role played by space – the smaller the geographical area to which the counterinsurgent can confine the insurgent, the better the chances for success. Last but not least, no counterinsurgency war can be truly won militarily. Politics will always be the deciding factor.