Research on behavior regulation was carried out after several months of social isolation, provoked by the pandemic, between the months of February and March 2020. In spring 2020, many higher education institutions began to introduce digital tools of education, remote learning, and distance teaching. The reaction during the first weeks and months was negative, but the experience of this remote regime of work and learning continued into the autumn semester due to COVID-19. This experience included the perceptions of new organizational approaches that were needed to regulate digital behavior as a specific type of strategy and choices made in the virtual space. This need was expressed in an understanding of the improvements to be implemented in the organization of educational processes at traditional institutions to efficiently apply the remote learning regime. Between December 2020 and March 2021, six focus groups were conducted to investigate if the regulation of behavior for remote work and learning (work for university administrative staff and academic teachers; studying for students) differed, with informal interviews also conducted to check the validity of the opinions formulated. The hypotheses of the lack of responsibility, and of iterative accomplishment of shorter and simpler tasks, were supported with the data obtained. The hypothesis on an imbalanced vision of mutual interests, and of the assessments of gains and costs of the remote activity, was confirmed. The hypothesis of the externalization of motivation was neither confirmed nor rejected, contradictory opinions were obtained, and, thus, further quantitative study is required. The conclusions based on the obtained results included support for improving the regulation mechanisms required to organize knowledge transfer when digital tools are applied at traditional educational institutions. To enhance the remote regime of learning, redesign and reorganization is necessary when considering the assistance needed by teachers and learners. Specific organizational efforts need to be implemented to restructure the teaching to shorter sequences, to stimulate the creativity of both teachers and learners (due to the readiness to experiment and the lack of critics, and constant access to online bases), and to identify the borders of the “sandbox” to clearly define and articulate the common rules of behavior.