Relevance of the research topic. The relevance of digital reality expertise that occurs under stochastic uncertainty is of great importance because we live in an era of Big Data when certainty is illusory, as exponential growth in information multiplies very quickly, resulting in staggering information flows. This set of stochastic information should be analyzed by experts armed with powerful computers, as well as armed with the systematic, structural, synergistic, analytical, quantitative, and philosophical thinking underlying Agile management, aimed at identifying patterns, formulating trends, and establishing laws . The purpose of the study is to conceptualize the examination of digital reality in the conditions of stochastic uncertainty in the context of nonlinear methodology, Agile management and computer modeling, to form a conceptual categorical apparatus that will help to reveal complex digital reality as a social phenomenon and dynamic process. Research objectives: 1) to analyze digital reality in the context of categories of certainty, uncertainty, stochastic uncertainty; 2) to define the essence of the concept of technological singularity; 3) to present the expertise of the sustainable development society; 4) to characterize the values of Enlightenment 2.0. Research methodology. The study uses forecasting and modeling techniques to help avoiding the mistakes and to succeed in all spheres of life. However, few people can predict what it is worth investing in, what new product is capable of conquering the market and what changes can be expected in the political arena. Even leading experts often think of certain things rather than analyze the possibilities of their occurrence. However, some experts are able to work reliable predictions, using modeling and forecasting methods, creating a formula of successful predictions that works in business, politics, international relations, which has a high degree of relevance to geopolitical forecasts. The result of the study. The concept of digital reality examination in the conditions of stochastic uncertainty is created, the digital reality is analyzed in the context of categories of certainty, uncertainty, stochastic uncertainty; the essence of the concept of technological singularity is defined; Sustainability Society expertise is presented; Enlightenment 2.0 values have been characterized. Practical recommendations. To use a holistic approach to fulfill the goals of a sustainable development society, from which both society, the state, international partners, and future generations will benefit.