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Western counterinsurgency doctrine proposes that cultural intelligence is an important requirement for those forces operating amidst the unfamiliar socio-political structures often found in distant conflict zones. Yet while the determination to understand the intricate nature of alien societies may appear a rational undertaking in such circumstances, Christian Tripodi argues that these endeavours rarely help deliver success. The frictions of war and the complex human, cultural and political 'terrain' of the operating environment render such efforts highly problematic. In their attempts to generate and instrumentalize local knowledge for the purpose of exerting influence and control, western military actors are drawn into the unwelcome realm of counterinsurgency as a form of political warfare. Their operating environment now becomes a space charged with phenomena that they rarely comprehend, rarely even see and which they struggle to exert any meaningful control over. All in pursuit of a victory that might literally mean nothing.

In his 1987 work 'Strategy: The Logic of War and Peace', Edward Luttwak described strategy as a field of activity characterised not only by an innately complex relationship between designs, actions, and outcomes, but so too by the frequent disparity between its theory and praxis. Similar observations on this subject have since been made by Richard K. Betts, Lawrence Freedman and Antulio Echavarria II. This article will use the Allied invasion of Sicily July-August 1943 as vehicle through which to test these theories against a signal event in the European theatre of World War Two. It will illustrate how Operation Husky and its aftermath are a paradigm of the confusing and often illogical course of events associated with the process of formulating strategy and waging war. In so doing it demonstrates the benefits of using strategic theory to illuminate events and so move beyond the often insular focus of campaign histories, and simultaneously reinforces the importance of military history in informing a theoretical understanding of strategy.

This article explores attempts by British colonial officials based in Aden to extend systems of political administration to the colony's tribal hinterland during the late interwar and early wartime period. Commencing initially with delicate attempts to recast faltering relations between tribal chiefs and their subjects, the policy would culminate a decade later with the despatch of British military units throughout the furthest extents of the protectorate in support of a range of direct political agreements with local rulers that would eventually set the conditions for federation. The intervening years featured a series of little-known debates among various officials on how precisely to cement British influence in the tribal areas, and the philosophy of administration to be pursued to that end. These would expose an element of confusion as to which techniques would best satisfy British policy, and reveal a preference on the part of some for the application of methods atypical of those used elsewhere under Colonial Office jurisdiction, and which drew their inspiration instead from systems of control used on India's volatile frontiers.

Over the past decade, Western military doctrines concerned with matters of irregular warfare and counterinsurgency have emphasised the requirement for properly 'understanding' the social, political and cultural environments in which those militaries may operate; the so-called human and socio-political 'terrain'. This has led to a number of advancements and initiatives designed to facilitate the way that militaries may enhance that understanding. One of those initiatives has been the emergence from within the British military of a doctrine – JDP 04 'Understanding' - designed for that purpose. Using that doctrine and other subsequent publications as a template, this article will examine the utility of 'understanding' for those commanders seeking to match military activities with political ends. It proposes that while any advances in understanding the operating environment are to be applauded, the 'understanding' of greatest importance is that relating to the feasibility of the strategic objectives at hand. If those objectives lack inherent feasibility, then the development of subordinate forms of understanding, particularly in relation to the socio-political dynamics of target societies, will likely only serve to slow the process of failure.