The Industrial Internet of Things (IIoT) and latest advancements in edge computing and analytics as machine learning and artificial intelligence are constantly reshaping the industrial maintenance sector. After the glorious leap from reactive and corrective interventions to timely scheduled preventive plans, condition-monitoring data and predictive algorithms, the maintenance professionals are about to integrate another important achievement in their portfolio. Prescriptive maintenance is introduced as the “maintenance of the future” and it spans across cognitive analytics and IIoT tools to “prescribe” to the machine a certain behavior, which will lead to its maximized performance. Why can predictive maintenance open the doors to the maintenance sector to enter the world of industry 5.0?