The article sheds light on the hot phase of the military conflict between Armenia and Azerbaijan that erupted at the end of September 2020. The key characteristic of the conflict is the use of the armed forces to defend different views and interests in an attempt to resolve smouldering territorial disputes. This phase will remain in history as the “Second Karabakh War” or “The Six-Week War.” From military analysts’ point of view, it is of interest with the application of advanced technologies to change the nature of modern warfare. On the one hand, the conflict is marked by a direct clash of different generations’ weapon systems, where the new generation’s technological weapon systems provide advantages in achieving strategic and tactical superiority. On the other hand, the war showed the implications of the national and military power of both countries in wartime. Improvements in weaponry brought the development of tactics, technics, and procedures in waging contemporary war. The main conclusions from the analysis relate to the mass operational usage of unmanned aerial vehicles and the respective development of ways of fighting at tactical, operational, and strategic levels.