The article substantiates the need to move from unified forms of developing cadets’ communicative self-efficacy to personalized, adaptive trajectories based on the synergetic understanding of personality as a self-organizing system in the specific conditions of a military university. The aim of the study was to develop and test a methodology for designing individual trajectories of communicative self-efficacy development in future officers based on synergetic principles and adaptive learning technologies. At the N Military Command School, 240 cadets of the 2nd–3rd years were examined in 2021–2023; they were randomly assigned to experimental and control groups of 120 people each, equivalent in key parameters. Standardized questionnaires on general self-efficacy, communicative social competence, communicative skills, an author’s situational confidence questionnaire, as well as a set of statistical methods (descriptive statistics, correlation, comparative and factor analysis in IBM SPSS Statistics 26.0) were used. The developed software and methodological complex included a diagnostic block (forming a multidimensional profile), a prognostic and design block (k-means clustering and generation of a baseline trajectory consisting of training, business game, case study, and simulation modules), and an adaptive-corrective block (microtesting, digital trace analysis, and automatic adjustment of the trajectory simulating the mechanisms of positive feedback and leading the individual to “bifurcation points” and a new attractor of high communicative self-efficacy). The results showed a statistically significant increase in the overall level of self-efficacy, initiative, argumentation skills, emotional stability, and constructive conflict resolution in the experimental group (average increase of 51.24% versus 8.72% in the control group, p 0.001), a dose-dependent relationship between the depth of trajectory completion and achieved results (r = 0.68–0.79, p 0.01), as well as a restructuring of the factorial structure of communicative self-efficacy into two integral factors: cognitive-instrumental confidence and affective-regulatory stability. The conclusion is made about the high efficiency and reproducibility of the proposed methodology as a tool of pedagogical engineering that ensures a phase transition of a cadet’s personality to more stable and productive communicative functioning and is suitable for replication in military and civilian professional education systems.