COVID-19 has substantially transformed societies and abundant literature has been developed. However, many important studies have been disseminated only in civil society and have not been systematized. Thus, the objective is to examine the challenges linked to the transformation of education and teaching described by non-academic research published in Chile during the first year and a half of the pandemic. The methodology is qualitative and document analysis is applied to 16 studies carried out by research centers, NGOs, foundations, and professional associations applied to educators and teachers in the school system. The results report five challenges associated with educational practices; conditions for remote education; student wellness and skills; teacher mental health; and contagion, classroom education and working conditions. In the conclusions, the challenges are perceived as an opportunity to create new meanings and relationships to build another future for education.