The purpose of this work is to envision the future of maintenance without forgetting the past and present of maintenance practices. Indeed, there is a big potential for maintenance, fostered by the promises of the Fourth Industrial Revolution. At the same time, there is still a widespread evidence of the state of practices leading to assert that maintenance is not yet advanced as it would be expected. Thus, comparing the vision supported by advanced maintenance systems, through the concepts of E-maintenance, Internet of Things and Cyber Physical Systems, with the evidences on the state of practices collected based on a sample of more than 300 industrial plants, we come up with a reflection on the advancement of maintenance management towards Smart Maintenance.