Military activities inevitably include an element of calculated risk taking, while at the same time the unnecessary taking of risks must be minimized. Within the context of the specific mission and situation, a number of factors relating to demographic variables, traits and beliefs may influence individual inclinations towards risk behaviour. The purpose of this study was to examine the relationship between such factors and individual risk propensity. Questionnaire data were gathered from two samples of Swedish soldiers and officers (N = 169) under contract for international missions. Data were analyzed using regression and cluster analyses. Our results show that demographic variables as well as traits and safety values constitute important explanatory factors of individual variations in risk propensity and sensation seeking. Men demonstrated a more skeptical view of safety measures and a higher risk propensity than women. Individuals with a higher degree of risk propensity and sensation seeking tendencies seem to be characterized by a lack of deliberation as well as a skeptical attitude towards safety issues. Furthermore, different “risk profiles” could be identified based on variations in risk propensity, impulsivity and safety values. The results highlight relevant aspects for identifying functional as well as non-functional risk takers. The implications should be of interest for recruiting processes as well as for training and leadership education.