The text investigates the issue of collaborating in new ways of thinking, being and acting in these times of paradigmatic transition, signaling some of the main contemporary dilemmas in education, with particular emphasis on the necessary training of teachers for their knowledge and appropriation of new technologies in the educational and school processes. After outlining these dilemmas, it addresses some aspects of the dynamics of the infant (cyber-infants) and school culture (multitasking), and their impact on the training and action of the teachers, who are “digital immigrants”, in contrast to their students, who are “digital natives”. We demonstrate that despite the ruptures and discontinuities in the contemporary educational practices, these situations do not create a complete and immediate split with the conducts of production and reproduction of knowledge and practice in the schools and educational spaces.