This monograph investigates the Italian Expedition in the Russian campaign during the Second World War from an operational perspective. It seeks to identify those factors relevant for practicing operational art that caused the collapse of the Italian forces in 1943. Specifically, the monograph identifies three main causes. First, at the political and strategic level, the Italian government did not provide the necessary support to the war in terms of political guidance, economic resources, and societal involvement. Second, at the operational level, in reflecting the widespread lack of resources and the absence of a centralized coordination among the services, the military forces were not able to adequately develop and modernize their structures, weapons, and equipment. Furthermore, an overall poor military culture affected the conduct of the operations. Third, ideological and cultural differences, an overall lack of trust, and the absence of primary coordination mechanisms undermined the relationship between Italian and German commands. The conclusion of the monograph depicts several lessons for current and future operational planners. The latter have to be ready to properly frame the operational environment, to consider the intangible values involved in the conflict, and to establish efficient coordination mechanisms within a coalition.