Officially, Windows 10’s free upgrade period ended six months ago. Unofficially, anyone who still wants to upgrade off a valid Windows 7, 8, or 8.1 license is free to do so. We covered how Microsoft hadn’t shut the upgrade program down not long after the update period ended on July 29, 2016 but we haven’t checked back to see if the servers were still up and running.
Over at ZDNet, Ed Bott tried updating an older Windows 7 system to Windows 10 and discovered the entire process still works perfectly. The solution is as simple as visiting Microsoft’s “Download Windows 10” page, grabbing a copy of the Windows 10 OS, and then installing the as an upgrade to an existing valid installation of Windows 7 / 8 / 8.1. Microsoft isn’t really commenting on this official loophole. But since the OS remains a free upgrade to anyone who uses Assistive Technologies (with absolutely zero attempt to validate that the user actually needs such technology), it’s fairly obvious what we’re seeing here: Microsoft may have officially ended its upgrade program, but it’s leaving the capability in place for anyone who discovers it independently.
And why not? It never made much sense for Microsoft to only give Windows 10 away for just 12 months. For all that the general public hated Microsoft’s nagware, it undeniably worked, driving Windows 10 adoption more quickly than any previous operating system. At the same time, however, Microsoft’s giveaway was also blamed for slowdowns in the PC market. For the first time in decades, consumers didn’t need to buy a new PC to get a new version of Windows — and historically, new PC purchases have been the way 90%+ of the market has gotten a new OS. Retail or OEM sales of Windows licenses through companies like Newegg have never been a major revenue source for Microsoft.
Windows10
If you use (or “use”) assistive technologies, Windows 10 is still a free upgrade indefinitely.
Microsoft may have set a 12-month deadline in the hopes of pushing people towards Windows 10 more quickly, or it may have reached an agreement with its various hardware partners that it wouldn’t keep advertising the free upgrade after a certain amount of time. Either way, the company has every reason to leave this loophole quietly open — every machine that upgrades is one more machine that’s now tied to Microsoft’s Windows-as-a-service delivery system.

Should you upgrade?

There are two facets to this question. If you’re still running on Vista or XP but have access to a legitimate Windows license that allows you to download and install Windows 10, yes, I’d argue in favor of upgrading (probably both your software and hardware, but that’s a different topic). There’s little reason to put in the effort to learn Windows 7 or 8 if you aren’t using them already, and Windows 10 can run fairly well, even on older hardware. Pre-Windows 7 operating systems are no longer receiving security updates, and that’s reason enough to advocate for a more recent OS.
If you’re running Windows 7 or 8.1, the question is a little murkier. These operating systems are supported through 2020 and 2023 for security updates, so you’ve got no objective reason to switch (at least, not for security reasons). I upgraded to Windows 10 at the tail end of the upgrade period and have had no particular issues with it, but while DirectX 12 support is nice, I can’t point to any features of the operating system that I really consider killer, either. Compared with Windows 7, it boots faster, some of the new UI elements are better, and the GUI is a little smoother. I don’t personally regret taking Microsoft’s upgrade offer, but I can’t really point to any grand improvements. Gamers have good reason to grab DX12, but for everyone else? It’s mostly a wash, at least for the next 2.5 years.