Abstract: Problem. The key concepts used to describe crisis phenomena in education – “contradiction”, “conflict”, “dilemma”, and “antinomy” – lack strict categorical definiteness and are often used as synonyms. There are no operational criteria for their empirical differentiation in normative texts and in the professional consciousness of teachers. The research is conducted within the context of late modernity philosophy. Aim. To substantiate the specific categorical status of pedagogical antinomy, to identify its essential features and an operational criterion of technological duality. Methods. A two-stage mixed-methods design: a theoretical stage (hermeneutic analysis of philosophical and pedagogical sources, categorical synthesis) and an empirical stage (content analysis of the Federal State Educational Standards for Basic General Education (FSES BGE) for 2010–2025, and a survey of 245 practicing teachers). Results. In the current version of the FSES BGE, 100 % of the identified contradictions satisfy the criteria of antinomy. The contradiction “upbringing – assessment” has transformed from a dilemma into an antinomy. Teachers recognise antinomies in only 46 % of cases (conflicts – 79 %, dilemmas – 61.4 %). A weak positive correlation was found between length of service, level of education, and the ability to identify antinomies. Conclusions. The introduced operational criterion of “technological duality” makes it possible to shift the identification of antinomy from the area of expert intuition to the status of an empirically diagnosable parameter. The developed conceptual and categorical framework (including the differentiation between antinomy, contradiction, and dilemma) is recommended for use in the expert evaluation of educational programs and in teacher professional development programs.