Aims: The purpose of the article is to highlight the anthropological dilemmas of contemporary philosophy related to the establishment of the information society. The global, local, and individual dimensions of informatization are projected onto modern human, which leads to his/her new positioning in the scientific and worldview picture of the world. The task of scientific research is to concretise the anthropological dilemmas of our time that are caused by information and technological transformations in society, namely: autonomy-dependence, traditionalism-innovation, and security-risk. Methodology: When the key research question is a dilemma, the most appropriate methodological philosophical approach is the dialectic one. It is based on the search for the truth of knowledge or conditions of development through contradictions and confrontations. At the same time, the entire arsenal of general scientific methods is also mostly oriented towards the dialectical format of research, actualising elements of comparative analysis, comparison, and modelling in the person interpretation in the current information and technological space. Results: The results of the article determine the dominance of pragmatic dimensions of efficiency in almost all anthropological dichotomies proposed in the study. Information and technology form a digital holistic system where the elimination of human-dimensional elements from the existential, epistemological, and axiological segments of the worldview paradigm of our time is initiated. Scientific Novelty: The scientific novelty of the study emphasises that classical anthropological constants such as autonomy, security, style, and traditions acquire contradictory characteristics in the permanent information and digital process of society development. Conclusion: Philosophy, by maintaining a constant methodological balance at the level of: contradiction-unity, makes another (in the cultural and historical dimension) attempt to resolve the problem of human positioning in the context of the dynamic development of a new type (in this case, a global information and technological) society.