The aim of this book is to examine the difficulty in planning and executing these transitions from the historical perspective of the German invasion of the Soviet Union in June 1941. In the wake of the initial invasion, the German Army began its struggle to secure a territory encompassing one million square miles and sixty-five million people while pacifying a growing partisan resistance. This book primarily focuses on the cognitive tension between decisive battle and the need to secure populations and infrastructure and persuade the occupied country to accept the transition from a defeated government to a new one. It also examines the formulation of resistance movements as complex adaptive systems, the potential of indigenous security forces and the influence of doctrine, cultural appreciation and interagency cooperation on operational-level transition planning.