With the recent developments of Industry 4.0 technologies, maintenance can be improved significantly by making it “smart”, proactive and even self-aware. This paper introduces a new cutting-edge interfacing technology that enables smart active remote maintenance right on the machine in real-time while allowing integration of smart automated decision making and Industrial Internet of Things to upgrade existing legacy equipment through latest Industry 4.0 technology. This interfacing technology enables remote sensing and actuation access to legacy equipment for smart maintenance by entirely non-intrusive means, i.e. the original equipment does not have to be modified. The design was implemented in a real-world manufacturing environment.