This article presents the problem of challenging the debtor's transactions made for the purpose of harming the property rights of creditors. The subject and scope of evidence has been studied in disputing such transactions. The problem of keeping the balance of interests of creditors and the debtor itself is considered. The problem of the presence of risks in entrepreneurial activity in the prism of the instability of civil turnover is investigated, in view of the possibility of challenging a wide range of actions of the debtor. The issue of determining the objective criteria for challenging transactions made with the aim of causing harm to creditors was considered.