The essence of the phenomenon of transgression in modern philosophical discourse is analyzed. The author defends the position that post-non-classical philosophy is built around the deconstruction of previous ideas, cultural processes and phenomena, for the definition of which the established terminology is no longer sufficient. That is why the phenomenon of transgression, which describes the state of transition and changes in phenomena, is becoming widespread. The purpose of the work is to conduct a phenomenological analysis of transgression within the framework of modern philosophical discourse. The presentation of the research material is based on the presentation of the transgression understanding basics by representatives of postmodern philosophy (M. Blanchot, M. Foucault, J. Bataille, J. Deleuze). The conducted research makes it possible to state the following. M. Blanchot talks about a person’s step towards transgression as a decision that expresses the inability of a person to stop, when changing himself. According to J. Bataille’s reasoning, transgression has a place to exist if there is a limit set aside for the functioning of anything, as a certain established norm, the violation of which should be considered as overcoming a certain taboo. Transgression, according to J. Bataille, does not destroy the prohibition itself, does not lead to the disappearance of prohibitions, norms, etc. According to M. Foucault’s opinion, transgression can and should become a kind of stone in the formation of a new culture of thinking, which replaces dialectical philosophy. Respectively, according to the concept of M. Foucault, transgression can be imagined as a reflection of the deep mechanisms of the evolutionary process. The dynamics of transgressive changes are uncertain, but they are capable of influencing social realities. It is concluded that modern society is becoming transgressive. The time of institutionalization of social structures, established norms and traditional values is fast-moving. Therefore, the use of the established paradigm of social ontology has its limitations. This approach simply does not allow us to understand the depth and essence of modern social changes. That is why within modern philosophy, an attempt to present an ontology of transgression is actualized, which allows not only to track changes in the social processes themselves, but also to move from one perspective of research to another, producing openness of interpretation, variability and ambiguity.