The territory that today corresponds to the Alentejo region, namely that which is near the border with the old Kingdom of Castile was, throughout the Middle Ages, one of the most important points of penetration in Portuguese territory, if not the most important. Thus, during the reign of King Fernando (1367-1383), the response capacity of the comarca (administrative circumscription) of Odiana will be put to the test. This work intends to show, through the analysis of the available primary sources, particularly the narrative ones, how royal power managed to solution problems related with the management and organization of war in this region. In a broader range we will observe the complexity of Portuguese and Castilian border relations, to some extent singular, albeit typical of the Late Middle Ages, based on a type of short-term military operations with the objective of weakening the economic power and authority of the enemy.