The paper reviews the existing approaches to using digital footprints in the digital learning environment. Monitoring digital footprints of university students can help to design smart learning environment and predict models of interaction between this environment and the user. The article covers the main analysis tools that can be applied to activity monitoring in LMS Moodle, including datasets as a convenient resource for distant learning. The authors studied authentication techniques that are based not on one’s knowledge but on the confirmation of one’s digital profile. The research results revealed some personal styles and patterns of cognitive behavior that reflect students’ work in the digital learning environment. The research results can be used to develop new psychological support of activity monitoring of the digital university environment, as well as to create new effective cognitive user-friendly interfaces.