Military education and training face a fundamental paradox, the demands for operational readiness are continuously increasing, while realistic training is constrained by safety, logistical, financial, and ethical considerations. In the context of artillery operations, particularly for Forward Observers (FO) and Joint Fires Observers (JFO), the ability to coordinate fire effectively and accurately is crucial for mission success and minimizing collateral damage. One of the new promising approaches is the use of Virtual Reality (VR) and Augmented Reality (AR) to train decision-making and tactical skills in a simulated environment. This paper discusses the development of a simulator that represents a significant advancement over previous generations of artillery trainers. Its main innovation lies in the integration of Artificial Intelligence (AI), which evaluates user performance in real time. This approach may contribute to increased training effectiveness and the personalization of performance assessment. The aim is to move closer to the vision of individualized, performance-oriented training that replaces universal and rigid instructional models—without endangering personnel safety, requiring the deployment of forces and assets in the field, or consuming material resources. Preliminary results confirm that AI-supported VR training can effectively reinforce observer skills while reducing dependence on live-fire exercises.