International literature in the field of education and teacher training has been widely focussed on reflection practices by embracing different connotations and perspective due to the object of the research interest, among the others: (i) the application of the reflection process in the didactical action (Dewey, 1033; Schön, 1987); (ii) the relation between reflection strategies and specific approaches to learning (Kolb, 1984); (iii) the contexts and the tasks which can facilitate reflection (Brown et al., 1989); (iv) the interplay among reflection, subject matters and professional skills (May, & Etkina, 2002). Starting from the assumption that in order to enable reflection processes, students need to be given opportunities to be actively involved in instructional activities designed as either self-reflection or social interaction (among peers and between the teacher and the group class) techniques/strategies, the overall reflection processes (in action) and outputs (on action) (Shon, 1987), when integrated fully within the course design, need to be widely explored in continuity with the transformation of the educational environments and their tools, factors which can deeply affect student course engagement and achievement. In online blended contexts where asynchronous activity is integrated with synchronous classes teachers needs to identify and apply strategies and tools to orientate students and, thus, overcome the risk of fragmentation (Han, & Hellis, 2020); a more systematic instructional design approach becomes of paramount importance to make the connections between tasks, feedback and course overall objectives meaningful for the student in a holistic perspective. The case-study here presented is based on the graduate course in "General Didactics" that took place fully online in the second semester of the academic year 2019-2020 at University of Macerata (Italy). The course is part of the first year curriculum of the "Socio-pedagogical Educator" degree in Education Sciences (three-year course). The collected data aims at emphasizing the impact of instructional design choices had on the activation of reflection processes in supporting students acquire a learning orientation (significativeness of the learning path); sustaining a culture of reflective practices in the specific professional area and profile; developing self-regulative strategies through different tasks and tools (e.g. individual writing/narrative tasks; group-based discussion activities, etc.).