This article examines the evolution of digital education in military pre-university learning environments, how it is regulated, implemented, and measured, how decision-making actors are involved in the process, and how the whole system will benefit from it. Also, comments from various relevant actors such as students, professors, and specialists involved in military preuniversity education in Romania will be compared, with the goal of emphasizing the effectiveness of students staying up to speed with current technological developments and being taught in this manner. Considering this presentation as part of an on-going PhD thesis, this article will only briefly present the current status regarding digital transformation of education in military high schools, the approach methodology, conclusions, and future activities to be further researched.