The work is devoted to the study of the specifics of the categories of "risk", "entrepreneurial risk", "business risk insurance" in Russian civil law, the main approaches to the definition of this concept are revealed. Entrepreneurial risk is considered as an objective and subjective category, where the legal assessment depends both on the specifics of the activity and on the entity itself. The novelty of the research lies in rethinking the nature of risk in the context of digitalization and economic instability. The author clarifies the civil law content of the category, distinguishes between the concepts of "entrepreneur's risk" and "entrepreneurial risk", and also suggests ways to improve insurance mechanisms. The article proves that the current ban on business risk insurance in favor of third parties does not meet the demands of the modern market (in particular, in holding structures and project financing). As a solution, it is proposed to legalize "cross-border" risk insurance within a group of companies, which will more effectively protect the interests of beneficiaries.