Confronting the Achilles Heel of the Free Windows 10 Upgrade

Posted on May 23, 2016 by Paul Thurrott in Windows 10 with 0

Confronting the Achilles Heel of the Free Windows 10 Upgrade

With just two months left for the free Windows 10 upgrade offer, Microsoft has to confront the secret problem that threatens to undermine this promotion: Many previously activated PCs will not successfully activate Windows 10 when the OS is later reinstalled.

This has happened to me at least twice, and I’ve heard from multiple readers who have been bitten by this problem as well. And once Windows 10 is no longer free for upgraders, it’s going to be even worse.

Here’s what happens. You have a PC that originally came with (or was upgraded to) Windows 7 or 8.1. And then you upgrade that PC to Windows 10, and it successfully activates because, let’s face it, the Windows 10 upgrade activation process is about as liberal as anything Microsoft has ever done. Success, right?

Maybe. That initial activation is supposed to provide you, as the owner of that PC, with the right to clean install Windows 10 on that PC, for free, for perpetuity.Or, more correctly and probably, for some amount of time. The “lifetime” of that PC, perhaps, which might logically be tied to the lifetime of the OS which originally shipped with it. Or something.

Regardless of the actual timing of this support, when you initially activate Windows 10 on any given PC, Microsoft is supposed to enter something I’ll call the machine ID into a cloud-based activation database. So when you (or some future owner of that PC) tries to activate Windows 10 later, the cloud database is checked, Microsoft verifies that the activation is allowed, and away you go.

It sounds like a great system. The problem is, it doesn’t always work.

I first raised this issue with Microsoft last fall when my (then-) desktop PC failed to activate on a clean install of Windows 10 despite having been previously activated. (The PC originally shipped with Windows 7.) At that time, Microsoft wasn’t able to figure out what happened, and PR simply provided me with a valid product key, which I assume is a nicety not extended to everyone.

So, hooray for me. But what about Microsoft’s customers?

The “solution” Microsoft offered at the time, which is the same solution they offer today, is to just reinstall the OS that came with the device, and then re-upgrade to Windows 10. That’s not much of a solution, though if you were going to go through that again, I’d recommend a PC Reset after its done for more of a clean install experience.

The problem, of course, is that many people no longer have a way to reinstall the original OS that came on a PC. And since Microsoft does not provide downloadable Windows 7 ISOs, as it does for Windows 10, many users would be left stranded.

Microsoft later offset this issue somewhat by letting customers activate Windows 10 using their PC’s Windows 7 or Windows 8.1 product key. That means you can now clean install Windows 10 on these PCs directly, with no need to install an older Windows version and then upgrade.

…. assuming of course you even have your Windows 7/8.1 product key. Which is the problem. In the past, your product key was always printed on a sticker on the PC’s body or power supply. But with modern PCs, that information is stored electronically in the BIOS/UEFI, and if Windows 10 can’t activate against that, you’re out of luck.

Many readers of this site are probably technical enough to recover from these kinds of problems. But this is the type of thing that will hit mainstream users hard, especially those who are among the 300 millionish people who upgraded to Windows 10 already. They simply don’t have a backup/recovery regimen that can save them from any potential issues.

If you are upgrading from Windows 7/8.1 to Windows 10, the advice in myWindows 10 Field Guide applies: Find your Windows product key, completely backup your PC, create a system repair disk, and separately back up your important data … before you upgrade. So many people don’t take these pragmatic steps, and these are the ones who may suffer because Microsoft can’t properly maintain a cloud database. I’ve written a lot about these topics, and if you can’t afford the book, please refer to my Complete Guide to Windows 10 for more information.

But I’d like Microsoft to figure out what’s happening here, and perhaps make the Windows 10 activation even more liberal on existing hardware going forward. It won’t hurt a thing, and it will help ease any hard feelings that would otherwise occur when a legally upgraded Windows 10 install no longer activates when the user decides they want a clean install. This isn’t rocket science, and it’s something that should just work.