COVID-19 lockdown measures adopted by governments in March 2020 have impacted our society as never happened before. The school system was not an exception. Interventions to allow students for distance learning through the support of 'old' (e.g. TV) or 'new' media (e.g. digital platforms) have been promoted, involving millions of students and teachers worldwide. This paper presents a study on school leaders and teachers' perceptions on the school levels of digital readiness through the comparison of their views before and during the lockdown. The participation in the EU project DETECT provided the context for exploring the school levels of digital readiness. Data were collected belonging to two different phases and allowing to investigate teachers' perceptions in using technologies for remote teaching. The school is living an unprecedent period where dramatic experiences are also disclosing new opportunities. Our study found that school had a strategy before the COVID-19 emergency, but it was too focused on infrastructures' acquisition, while the development of competences on the side of both teachers and students requires an investment in long-term training, up to the point of reshaping the current teaching practices and also planning for interdisciplinary educational activities addressed to the students.