The circular economy is an economy that meets sustainable requirements, and that advocates a new paradigm, the paradigm of regeneration. This paradigm allows creating new businesses, new jobs and new skills all along about the product lifecycle. This is especially the case for maintenance and retirement processes. Indeed, these processes are the regeneration core. Those of retirements do not sum up to destructuring process but match also with repair, reuse and disassembly processes. As for maintenance, it becomes the cornerstone of all this. Through all its current skills, it allows managing and optimizing the regeneration by deciding when to stop a use and where studied items should go. Besides, maintenance must adapt to the regeneration. In other words, tools and methods used by maintenance can be able to maintain the regeneration potential of an item, and thus, create new jobs and experts. The purpose of this paper is to highlight the major challenges brought by the paradigm of regeneration to maintenance.