This article presents the development of version 2.0 of a technological platform for evaluating school engagement in Chile, Colombia, Peru, Uruguay and Spain. The platform contains instruments for measuring school engagement and contextual factors, reports of results, and educational resources. This aims to accompany educational paths, provide timely supports, and promote school retention. The development of the platform has been incremental based on associated R&D projects. It has been recognized by the UNESCO Chair in Children, Youth, Education and Society and it offers the opportunity to be used in other countries, at a time when school dropout is a concern of special relevance in Latin American and global level.