In the article authors examine modern ways of expression of will of the parties in the context of digital transformation and their impact on the practice of law enforcement. Specific attention is paid to such aspects as digitalization, smart contracts, click-wrap, browse-wrap and shrink-wrap agreements, as well as the use of biometric identification for transactions. A new trend - the use of emoji as a substitute for a signature in a contract - is also analyzed. The article examines foreign and domestic judicial practice, which testifies to the legal significance of emojis. Special attention is paid to cybersecurity issues in the context of digital transactions. The author's vision of understanding smart contracts, click-wrap agreements, browse-wrap agreements, shrink-wrap agreements is proposed. Benefits and risks of using these tools are analyzed and recommendations for ensuring the legal validity, security and efficiency of such digital transactions are offered. There is a trend of multiple growth of new digital phenomena that deserve legal regulation, keeping pace with the rapid penetration of technologies into the sphere of property relations, revolutionizing it with fundamentally new business opportunities. They have created a range of new categories that, to one degree or another, become objects of legal regulation or deserve to become them - "big data", "blockchains", "digital assets", "digital rights" and others. Digital transformation, integrating into entrepreneurial activity, qualitatively changes it. Often, the entire process from the moment of conclusion of the transaction to its completion is carried out electronically. For the most effective economic cooperation, it is necessary to create fast and flexible ways to resolve disputes. It is possible to achieve these goals by integrating modern information and telecommunication technologies into this process. The general trend in the dispute resolution process is the transition to electronic form. The authors analyze the domestic and foreign literature devoted to identifying the role and importance of law in regulating relations of digitalization and conclude that legal science has begun a large-scale and in-depth study of the content and methods of regulating relations regarding artificial intelligence.