Abstract: The article substantiates the methodological tools for assessing the entropic development of enterprises in a transcendental economic environment characterized by a high level of uncertainty, turbulence and nonlinear changes. The essence of entropic development is revealed as an integral characteristic of disorganization, instability and stochasticity of business processes that affect the efficiency and stability of the enterprise. A comprehensive approach to assessing entropy is proposed, which combines systemic, process, quantitative and qualitative methodological approaches, which allows identifying sources of entropic disturbances in the financial, information, organizational, production and marketing spheres of the enterprise. The feasibility of integrating elements of information theory, synergetics, fractal geometry and fuzzy modeling for in-depth analysis of complex dynamic development processes is substantiated. Special attention is paid to building a mathematical model of entropic development of an enterprise based on a system of differential equations of the Volterra–Lotka type, adapted to economic conditions. The proposed model allows us to study the interaction of profitability and entropic factors, analyze development trajectories, determine dynamic equilibrium points and evaluate cyclical fluctuations as manifestations of entropic instability. A linear analysis of the system behavior around the equilibrium point is performed and the possibility of quantitative assessment of economic risk as a measure of entropic volatility is substantiated. It is proven that the application of the proposed methodological tools creates a basis for the formation of adaptive and antifragile management strategies aimed at reducing the destructive impact of entropy and ensuring sustainable and innovative development of enterprises in the long term