The recent advances in digital technologies are revolutionizing the industrial landscape. Maintenance is one of the functions that may benefit from the opportunities that emerge with the digital transformation of industrial processes. Nevertheless, until now very few research papers investigated on what digitalized manufacturing entails for maintenance organizations along both technical and social dimensions. The aim of this paper is to investigate the vision of the future of Maintenance within the industry 4.0 and to show empirical evidence on how manufacturing companies are approaching the digital transformation process of maintenance. An empirical investigation was developed through multiple case-study involving nine manufacturing companies in Italy. Findings emerge about the main perceived challenges by companies for the success of digital transformation of maintenance as well as the technological and organizational mechanisms that are used in ongoing innovative Maintenance projects.