The article examines the problem of organizing distance learning in the conditions of uncertainty and the forced transition of teachers and students to online interaction. The situation that has arisen is viewed as a natural experiment the education system finds itself in requiring an understanding of its results at a certain stage. A theoretical analysis of the most popular distance learning organization technology implemented in Russian universities under current conditions (the coronavirus pandemic) is conducted and a critical evaluation of the obtained initial results of the readiness of higher education system to transition into the new digital education reality is provided. The discovered problems of distance learning include: the insufficient level of teachers’ digital tolerance and the lack of necessary competencies in them; the psycho-emotional instability of the online interaction participants; low learning motivation and the level of students’ practical skills; the lack of a universal digital platform for the organization of activity of all participants of the learning process. The perspectives for solving the aforementioned problems and priority directions in the improvement of this form of education are established, specifically: the technological direction (the formation of teachers’ ability to create online courses and effectively combine the functions of different digital platforms); the methodical direction (the formation of a set of professional and personal qualities necessary to effectively address professional tasks and expansion of the set of methods and means of organizing students’ activity considering the conditions of online interaction); the psychological dimension (teachers’ awareness of the need for self-improvement in the sphere of digital technologies and the formation of interest in learning and satisfaction with the process and results of distance learning in students). The identified areas are considered as risks the consideration of which in educational activities will make the distance learning process flexible and manageable.