In the need to resort to distance learning, due to the current health emergency, our school system has revealed itself only partially accustomed to the use of technologies. Eight and a half million students and 800,000 teachers were faced for the first time with ways of learning and teaching entirely based on IT tools. For 82% of Italian schools it was the very first experience with online lessons. With an average age of 51, Italian teachers are the oldest in the world. This means that they can count on a solid teaching experience and on the rooted belief that education can make the difference in a student’s life, no matter which social class he/she belongs to. Yet the lack of native digital skills is widespread, together with a strong resistance to change. Broadly speaking, teachers consider technology detrimental to their skills and role and would do anything to avoid the revolution brought about by IT and online classes, considered them tiring, boring, impoverished and distant from the model they have in mind (even if it dates to the 1930s). As a teacher myself, I am perfectly aware of the unique heritage of their outstanding cultural background but at the same time I can witness that traditional academic classes still prevail: I teach, you learn. I assess and you’re successful if you repeat my words as faithfully as possible. The double-edged challenge we are to face is that of helping teachers embrace risk and change, making them protagonists of this change, preserving the righteous pride in their profession, avoiding to make them feel teaching machines, keeping their ability to be inclusive and to foster social promotion.