The question that underlies this text is to think about the professional re-enchantment of veteran teachers in the context of a project that aimed to promote ICT as a vehicle for improving curriculum agency among these professionals, diminishing the intergenerational gap they face in their classrooms and in their schools. Rekindle+ 50–Digital migrations and curricular innovation: giving new meaning to experience and rekindle teaching profession after 50, is a project that invested in an idea of training for professional development that aims to place teachers and their curricular decisions, assisted by ICT devices, at the heart of the training action. The chapter provides an overview concerning discourses about innovation, curriculum and technologies that challenge veteran teachers in Portugal, describes, briefly, the Rekindle+ 50 project in its attempt to study the conditions of professional re-enchantement of veteran teachers, and presents the preliminary results of the project.