The COVID-19 pandemic launched a challenge on the education system and required schools to make organizational changes in order to continue serving the local community. Essential to this process are support teachers who play a key role as agents of change. Despite their role, the perspectives, desires, and needs of these teachers have since been neglected, despite their centrality in contemporary Italy. Accordingly, the specific aim of this study revolves around supporting teachers’ experiences with digital technologies (i.e., learning applications, telecommunication media, and interactive devices) within a pandemic context, especially technologies used to maintain the educational bond with students with disabilities. Attuned to an interpretative paradigm, this qualitative research has an ethnographic design, which was implemented in a secondary school in a Northern Italian city. Throughout the article, we discuss the three main drawbacks found in fieldwork: (i) the prevailing change in bureaucratic management; (ii) the pervading mind–body binarism in teaching; and (iii) a long-term vision for inclusion being subject to a passive logic of adaptation. Finally, we reflect on some emerging implications. The first points to a necessary move from a rationalistic school management to an alternative model focused more on guaranteeing social justice among educational stakeholders. The second is that the very introduction of a new technology should be aimed at engaging actors whose work has been invisible to date in a school setting to empower them as key agents for change. The third suggests that, to overcome community disaggregation and mind-body binarism, a teacher-researcher figure is needed, a figure with holistic skills in addition to those of a technical nature delivered by institutional training programs.