Windows 7 is exiting support on the 14th January 2020, and in theory, this would mean anyone still stuck on Windows 7 will need to pay $120 to upgrade to the newest OS.
In practice, however, it appears that if you do an in-place upgrade using the Media Creation tool you will be able to activate your new Windows 10 installation without any issue (note this does not work with a clean install).
According to someone who claims to be a Microsoft employee this is by design, Microsoft prefers to have home users on Windows 10, even if it is technically on an unpaid copy. Microsoft did offer a free upgrade to Windows 10 in 2016, which supposedly ended, but Microsoft never bothered to fix the MCT loophole despite it being widely exploited through the years.
Cokerobot writes on Reddit:
Well, I guess the cat’s out of the bag…
I work at Microsoft and have been since before the Windows 10 launch. That whole “free” upgrade for a year was fully marketing fluff. After the cut off happened, the direction given was that it requires a paid license HOWEVER, this was brought up by the brick and mortar stores that they were doing simple clock changes on customer devices during the upgrade challenge to get around it and then ultimately it was clear two years later that anything Windows 7 and up would go to 10 fully activated and still to this day.
WDG didn’t care pretty much at all because Terry Meyerson at the time cared more about his upgrade stats than license revenue as Windows isn’t Microsoft’s cash cow anymore. It’s the same stance back in the day where Microsoft would allow Windows Updates on pirated copies of Windows 7 as the bigger picture was to thwart security threats based from those copies.
You still can do this no problem, however careful, do an upgrade keeping everything as if you choose to yeet everything and start fresh, you lose your free upgrade. That old 7 license converts to a 10 digital license and from there you can clean install no problem. As for audits, this mainly is for volume licensing than anything. An SMB with 10-200 Windows 7 machines that were OEM licensed don’t really matter. If you try this with 1,000 computers, iffy. At the end of the day, Microsoft had four years to close that loophole and never did so if worse came to worse, you could technically go through legal avenues as the EULA for 10 literally doesn’t have a clause for this at all. You can’t shit on someone taking advantage of an activation workaround when you as the manufacturer never closed it.
Whether CokeRobot is credible or not, the fact is that you can upgrade to Windows 10 from Windows 7 using the Media Creation Tool relatively easily, and if you have been worrying about the impending end of support of Windows 7, with good back-ups of your data you really have nothing to lose from attempting the free upgrade to Windows 10 before Microsoft closes the loophole.