The key possibilities of digital technologies for organization of the collaborative learning activities are highlighted, including increase of the level of interactivity and personalization of group learning, as well as promoting intercultural cooperation. Main challenges, arising as a result of implementation of the collaborative learning in a digital format are identified and systematized, including technical constraints, communication barriers, organizational difficulties, pedagogical aspects, psychological and social factors, as well as problems related to the level of digital competence of the educational process participants. A number of factors that significantly affect the effectiveness of collaborative learning activities in a digital format are identified, including the clarity of learning goals, the structure of tasks, the role of the teacher, the quality of digital tools and group dynamics. Based on the analysis carried out, practical recommendations have been developed for teachers and administrators of educational institutions regarding the design and implementation of effective models of collaborative learning in a digital environment. Methodological approaches to group work organization, using digital tools, and evaluating the results of collaborative learning activities are proposed. Ways to overcome the identified challenges through the development of digital competence, optimization of technical infrastructure and implementation of appropriate organizational solutions are outlined.