This article offers future perspectives on how technology could complement situation awareness (SA) and dynamic decision-making (DDM) training. It draws on three cases conducted at the Estonian Academy of Security Sciences (EASS) between 2017 and 2024 to illustrate the different technologies used to measure SA and DDM. The first case focuses on video-based measurement of SA, the second on the use of virtual reality (VR) to measure DDM, and the third on augmented reality (AR) to measure SA. The results show that video-based and AR methods primarily allow the measurement of actual SA, as participants follow programmed paths without offering their own DDM solutions. VR technology is most effective for DDM training and makes it possible to interact with the environment. However, it requires feedback from trainers, making it more labor intensive and expensive compared to video-based measurement of SA. Based on the analysis of the cases, the article suggests that further integration of technology into training, particularly DDM training, will become increasingly complex for trainers. That is due to the challenges of selecting the appropriate tools as well as issues related to access and usability of technology. To overcome these challenges, more research on the use of educational technology is recommended to identify suitable tools and improve the effectiveness of D-learning.