The article describes the current rules and case law on drawing up wills in Russia. The author argues that the literal approach and the lack of stop-gap rules are hardly compatible with succession law policy. Due to the problem of correct interpretation of a will, we cannot talk about real testamentary freedom. The situations with wills are usually complicated because the authors are absent. As for interpretation of wills, the contemporary landscape shows that most of European countries prefer intentional approach: when the interpreter would take into account the indirect extrinsic evidence. Speaking of Russian approach, the priority is given to the literal interpretation: the methodological recommendations on drawing up the rights of inheritance clarify that in order to understand the literal meaning of words and phrases in the will, their plain meaning should be determined, and when interpreting the legal terms, their meaning set forth by the legislator in the corresponding legal instrument shall be used. On the base of comparative research and empirical experience “new” intentional approach is proposed.