Digital skills are one of the most contested key competences in the educational sphere. On the one hand, they have become essential to guarantee standards of educational quality and progress, on the other hand they tend to further hamper educational inequalities among the contemporary highly-diversified student population. This paper ties into these premises with a case study located in Turin, Italy based on 19 teachers and educators from all school levels (primary, lower-secondary and upper-secondary education) to highlight the transformation of needs and challenges related to the different phases of the life cycle of students. Three main issues were investigated from a comparative perspective among the study participants: (1) the coherence of their knowledge regarding opportunities and the challenges of digitalization; (2) their skills to implement digital instruments in their working context; and (3) their attitude towards the transfer of potential benefits that enhance learning outcomes through digital instruments. Findings suggest that high-quality and effective staff formation represents one of the most critical issues when talking about digitality in the educational sphere. A chronic lack of time for training, the ongoing work in emergency conditions, the heterogenous institutional endowment with technical devices (PCs, digital infrastructure, etc.), and the suspicion towards the benefits of digitality in the classroom are some of the major barriers to the forwarding of digital competences as a set of skills, knowledge and attitudes within the educational context.