In this article, we explore the role of two narrow personality traits, Sensation Seeking and Need for Structure, in soldiers’ situational perception in a military task-environment. In the first study, we assess the psychometric qualities of the personality inventories, Sensation Seeking Scale-V and Personal Need for Structure, in an Estonian military sample. In the second study, we explore how these traits are related to soldiers’ perception of complexity (predictability) and potential harms involved (riskiness; defined as situation structure) in two field exercise tasks. We found that both of the explored personality traits are significantly and inversely related with soldiers’ perception of situation structure in a military environment. Implications for personnel selection, training, and performance of military organizations are discussed.