In the presented paper it is investigated the influence of the subjective perception of the objectively existing security values upon the security measures and indicators in the framework of the subjective entropy maximum principle. The subjective analysis theory entropy paradigm makes it possible to consider the security system based upon dynamic parameters as an active system governed by an individual (active element of the managerial system) with the help of her/his individual subjective preferences optimal distributions obtained in conditions of the available situation multi-alternativeness and those achievable alternatives presence, as well as the active system active element’s individual subjective preferences uncertainty. The described approach takes into account the simple two-alternative security situation in regards with the objectively existing effectiveness functions, related to security measures, in the view of a controlled parameter and a combination of it with its rate as the ratio. It is obtained the expressions for the objective functional extremal functions of the effectiveness and preferences, mathematically explicitly visualizing the security situation and allowing taking a good choice. The ideas of the required proper governing, managing, and control methods choice optimization with respect to only 2 alternative objective effectiveness functions arguments might be simple; nevertheless, increasing the number of parameters and further complication of the problem setting will not change the principle of the problem solution. This study is rather comparative. The significance and value of the study becomes clear in comparison with the theoretical results in the entropy paradigm field. Herein the solution obtained in the explicit view based upon the integral form objective functional. Such kind of dynamic optimization was not modeled in the background works.