Training and measurement of situation awareness (SA) in a dynamic decision-making context is a complex task and depends on personal factors as well as time, space, and situation. Therefore, to measure first-level incident commanders’ SA several authentic and immersive virtual simulations of rescue incidents should be used. In this paper, we report on Effective Command and the dynamic decision-making assessment methodology as a theoretical framework for SA assessment and implementation of virtual reality software using sixteen different virtual simulations in an organization. First, we report four aspects needed to be implemented for virtual simulation-based assessment of SA. Next, we analysed the differences between three SA ascending levels: perception, comprehension, and prediction that might be influenced by the scenario storyline. According to prior research, we would expect the difficulty of the three SA levels to be in ascending order and we evaluated that by analysing N = 665 assessment results. We confirmed such an ascending order for most scenarios, and we also identified these scenarios for which this assumption was not met. Finally, we discuss the possibilities of analysing the scenario-based SA level differences in the future when assessing SA with more automated measures. We argue that by improving the assessment of SA, we can foster the training possibilities for incident commanders’ dynamic decision-making.