Technology enhanced learning becomes the commonness in the nowadays educational process. Modern information systems open new departure in teaching and learning methods, enhance learners’ critical thinking, reflection and competence development, broaden the ways in which the students are engaged in class activities, and as a result, lead up to the changes in existing educational paradigms. Latter findings acquired from the piloting of the experimental information system, based on multiscreen, so-called eBig3, approach, showed positive results in learners involvement into knowledge acquisition process by using of e-, t- and m-technology. This course demonstrated also another system’s feature which has let its users had substantial benefit – the diminished dropout rate. It has spurred researchers on further development of the user-friendly adaptive system equipped with appropriate feedback generating tools. This paper observes possible solutions to improve the system’s messaging tool and make it more intelligent. Conceptual design and algorithmic model of the proposed adaptive integrated technological system with the integrated feedback tool is introduced. The idea reposes on the observations that system user behaviours appeared in patterns and that these patterns reappeared with a number of learners; accordingly, they might be separated into a number of data sets and, based on that, several user groups depending on their behaviour patterns could be formed. Proposed system will have to generate appropriate messages from the message repository to corresponding user. This messaging system will be able to send both SMSs and emails to learners and course tutors. It will also support collaborative activities within e-learning environment.