During the years there has been an increasing number of one-to-one programs around the world. In such programs all students are equipped with portable devices, such as laptops, tablets, smartphones for learning purposes. Even if these initiatives are increasing, our knowledge of the impact of such digital transformation of education is still little studied. Based on data from a three years longitudinal study on a large-scale implementation of Chromebooks in a municipality, this paper highlights teachers’ experiences. Key findings suggest that this initiative has been successful when it comes to the administrative and technical implementation of the Chromebooks, but there is still a way to go to transform pedagogical practices to enhance student-active learning supported by the Chromebooks.