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It looks like Microsoft is starting to make some attempt at closing the Windows 10 Free Upgrade loopholes. The Media Creation Tool, which provides detailed options for upgrading, now prompts Windows 7 or Windows 8 systems for a product key. The Media Creation Tool takes into consideration, users, who might have downgraded a previously installed and activated Windows 10 installation; by giving them the option to reinstall Windows 10, exempting them from the product key requirements. The new Digital License function attaches a Windows 10 license to the machine, permitting unlimited reinstalls without the need to have a product key or contact support to get the software reactivated. When users download the download the Windows 10 Media Creation Tool, they will see the following screen as usual. If the option to Upgrade this PC now is selected, the user will be prompted the enter a valid Windows 10 product key. Any attempts to enter a Windows 7 or Windows 8 product key will be invalidated: A new option has been added to the setup screen for users reinstalling Windows 10 on a previously installed and activated system. If your system has a Digital License attached to it, Windows 10 will automatically upgraded: Users can still circumvent the prompt for a product key by selecting the option Create installation media for another PC. There is another step users will have to follow in order to avoid being prompted to enter a product key. Even when installing from ISO, users can be prompted for a product key if the option Download and install updates (recommended) is selected. Instead, users should select the option Not at the moment. This will permit the upgrade to continue. I am sure Microsoft is working on a more concrete solution to ultimately end the free upgrade offer. In the mean time, you can still get it while door slowly closes. Thanks to Philip Yip of DellReinstallGuide for the tip!