In recent years the great powers of the West—primarily the US and UK—have most often been relegated to fighting “small wars,” rather than the great confrontational battles for which they once prepared. It has been a difficult process, with some conflicts increasingly being seen as unwinnable, or at least not worth the effort in treasure and blood, even as the geopolitical structure of the world appears to slip. It is thus worth paying heed now, to the experiences of another power which once encountered the same problems. This work examines the German analysis to the problem, covering their experiences from the Napoleonic era to the Third Reich. Though the latter regime, the most despicable in history, needed to be destroyed by US/UK conventional force, as well as that of the Soviets, the German military meantime provided analysis to the question of grassroots—as opposed to great-power—warfare. This work is built around the historical analysis titled Kleinkrieg, provided to the German High Command by Arthur Earhardt in 1935 (republished in 1942 and 1943) which examined insurgencies from French-occupied Spain to recurrent problems in the Balkans. It also calls upon the Bandenbekampfung (Fighting the Guerilla Bands) document provided to Germany’s OKW in 1944.