The dynamics and uncertainty of business environment greatly complicate the decision‑making processes for the company’s executives and managers. That’s especially important if they do not possess high‑quality and reliable information database on the state of internal and external environment. Thus, the purpose of this paper is the development of specialized probability diagnostic techniques for enterprise operating under the conditions of uncertainty. Two basic research methods were used in our research. Firstly, the study was conducted on the basis of review and analysis of specialized literature in the field of information diagnostic support of enterprises under the conditions of uncertainty. This allowed us to propose our own solution in this regard. Secondly, the developed diagnostic method was tested on one of the Ukrainian enterprises. The obtained results enabled us to determine the most probable threat to the functioning of the entity. We also conducted the quantitative assessment of its possible impact on the performance of the company. Therefore, suggested diagnostic techniques aim at forming the grounded information basis about different potential changes of business environment, as well as the enough time reserve, and can be recommended for the company’s managers during the decision‑making process under the conditions of uncertainty.