In this chapter, we elaborate on effects of recently induced digitalization of teaching, and consequently on innovative learning. A series of workshops on using digital tools in the teaching process—performed by teachers for teachers—was used to conduct a two-level analysis on how digitally supported teaching is performed. In the first level, a teachers Delphi analysis was performed, in the second level, we observed teacher performance in the role of learners, examining the user experience of multiple digitally supported teaching technologies. The study reveals that only some elements of innovative learning, i.e. understanding, commenting and providing feedback, modifying the environment and upgrading the learning content were positively influenced by digital technology. The proposed text can provide value-added for teachers in preparing their on-site and on-line courses; furthermore, it provides educational organization backgrounds on how to deliver adequate support for their staff, and finally: it gives learners an insight into how to participate in an innovative course.