This article raises the problem of society’s and individuals’ trust in the law during the digital transformation. It identifies factors that in many ways lead to decreased trust in the law. These factors include geopolitical crises and the changes the world experienced during the pandemic, as well as processes of poorer quality rulemaking, public administration, legal drafting and enforcement. It also identifies reasons why the law lags behind the realities of widespread use of new digital technologies in the XXI century, in which the number of gaps in the legal regulation system becomes critical for jurisprudence, legal theory, society and the state. It has been found that increasing information pressure on the individual and the individual’s openness and defenselessness to information flows, as well as stress and the infodemic, particularly during a pandemic and geopolitical crisis, destroy the ability to shape critical thinking. Due to overload, they deprive people of skills for effectively learning something new and developing creatively. Also, the more time the individual spends in the information space, subjected to powerful targeting technologies, the less right he or she has to choose. This is particularly the case now as the world is dominated by a couple dozen global digital platforms that provide people and small and medium business with an ever-expanding range of services, which means they no longer have the economic ability to choose other, alternative solutions. The changes that have occurred in the system of people being forced to work remotely, “regulatory administration”, the use of people’s fear and confusion, have questioned the authority of the law. The article concludes that identifying information law’s place in Russia and the modern world, including issues of the need to systematize information legislation for the country and society at a time when digital data are becoming the basis for a growing number of social interactions, seems to be one of the important processes to boost trust in the law as a social regulator. The article raises issues of the legal regulation of the circulation of big data, the Internet of things, artificial intelligence and other digital technologies. It analyzes a number of legal issues, including the generation of consistent hierarchical legal terminology for the Internet of things and a common vision of the system of IoT legal issues requiring new or modified solutions in light of industry specifics and the current state of the regulatory framework. At the current stage of humanity’s development, the “right to reject the use of digital technologies” could be a rational tool to strike a balance between individuals’ rights and the public interest. Therefore, it will be important for achieving the goals of information law to create a system that protects the rights of those who are unable, unwilling or afraid to use new sophisticated technological solutions such as various cutting-edge digital technologies, including artificial intelligence technologies.