The conducted research was linked to the theme ‘Military Geography and Geology Study of the First World War Sites in the Province of Belluno’ and emerged from the Ph.D. scholarship awarded by the Foundation for University and High Culture in the Province of Belluno. The Province of Belluno, located in the southern eastern Alps, is an Italian administrative division. Its territory, which is almost entirely mountainous, was the site of many battles between the Austro-Hungarian Empire and the Kingdom of Italy during the First World War. Despite the enormous historiography on the First World War’s Italian front, few studies have examined how the geography of the Alps influenced the War. This thesis studied the influence of geography on the Eastern Tyrol front in the First World War, particularly the geography of the Dolomites front (which in part corresponds to the territory of the Province of Belluno). To reach this aim, the research produced four papers. The first paper was a bibliographical review of the Cadore offensive’s failure and provided a synthesis of opinions surrounding the involved factors and origins, which in turn led to the other three papers. Following the bibliographical review, the second paper focused on General Cadorna’s military assessments for the Cadore offensive’s geography. In accordance with some authors (i.e., Botti, 1991; Isnenghi and Rochat, 2008), the results suggest that possibly Cadorna did not fully consider the difficulties connected to the geography. The third and fourth papers, on the base of the perspective traced by the first paper, aimed to provide a better characterization of the military value of terrain, producing an empirical qualitative and quantitative analysis of physical geography and its influence on military operations. The third paper studied the influence of geomorphology on the Cadore offensive. To reach this purpose, a geomorphological and a military history map were made for four of the most important areas in the Dolomites front. In particular, the steep and high valleys’ sides, part of the unique geomorphology of the Dolomites, determined unassailable positions from where the defenders, with protected and sometime relatively accessible rear lines, precluded the use of the valley, due to the visual control and the use of crossfire. From that point of view, topography, as the result of the particular morphogenetic processes which took place in the region, can be considered as one of the main geographical aspects that controlled the development and the outcomes of battles in the Dolomites front. The fourth paper used a cost distance analysis, a Geographic Information System (GIS) tool, in order to assess the obstacle to trafficability in Eastern Tyrol. The obstacle to trafficability can be considered one of the most important properties through which terrain influences war in mountainous countries (Clausewitz, 1832). The results demonstrated that the decision to defend the Tyrol Defence Line (TDL; i.e., the line chosen for the defence of the Tyrol region by Austria-Hungary) instead of the former political border did not reduced the perimeter to be defended. Thus, from this perspective, the shorter length of the TDL cannot be considered a military advantage, as other authors have inferred (e.g., Lichem, 1995).