The article presents the results of the research of the problem of differentiation of general and special grounds for challenging debtors’ transactions in bankruptcy cases. Based on the analysis of legal acts, materials of court practice and positions of the Supreme Court of the Russian Federation, the author has established specific features of law enforce ment of general and special (bankruptcy) grounds for challenging transactions of an insolvent debtor. On the example of judicial practice materials the article argues the author’s position that the problem of application in practice of these grounds remains relevant for the courts due to the fact that the legislation does not reveal sufficient criteria for differentiating these grounds. Despite the impossibility of applying general and special grounds simultaneously, cases of their joint use arise in court practice. These aspects give rise to legal uncertainty. In this connection, more detailed regulation of specific features and grounds for application of bankruptcy grounds for challenging a debtor’s transactions is required. Prospects of the present study consist in substantiation of proposals on introduction of amendments and additions to the Federal Law dated October 26, 2002 No. 127-FZ “On Insolvency (Bankruptcy)” taking into account the analysis of judicial practice materials.