New Windows 10 beta build 14371 introduces mysterious Activation Troubleshooter

There's a new twist in the Windows licensing maze, and Microsoft has provided frustratingly few details

New Windows 10 beta build 14371 introduces mysterious 'Activation Troubleshooter'
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Yesterday afternoon Microsoft released a new beta build of Windows 10 to the Insider Fast ring, 14371.0.rs1_release.160617-1723. We know it isn't a final build or official release candidate because of the telltale watermark on the desktop and expiration date (type winver in Cortana). That's about all we know for sure at this point. 

The pace of beta versions has been breathtaking: There was 14366, on June 14, with the LastPass Edge extension; 14367, on June 16, with the Start Fresh option; and now 14371, on June 22, brings us the Activation Troubleshooter. In each case, we've had lots of fixed bugs, a few lingering known problems, and very little visible change -- as befits the final stages of a beta.

Discussion of the Activation Troubleshooter starts with spokesperson Dona Sarkar's description on the build 14371 announcement page:

Starting with this Insider Preview build, we're introducing the Activation Troubleshooter that will help you address most commonly encountered activation issues on Genuine Windows devices including those caused by hardware changes. For example -- if your device has a digital license (formerly called "digital entitlement") for Windows 10 Pro from a previously installed activated Windows 10 build but you accidentally re-installed Windows 10 Home on such a device, the troubleshooter will automatically guide you through upgrading to Windows 10 Pro and activate Windows…

We are also introducing the ability to link your Microsoft account (MSA) to the activation digital license with this Insider Preview build. If you already used an MSA to log in to your activated Windows 10 Home or Pro device, your MSA will be automatically linked. You can use this MSA linked digital license to re-activate your Genuine Windows 10 device by running the Activation troubleshooter, if you run into Activation issues caused by hardware changes.

There's also a lengthy discussion, with screenshots, on the Win10 Insider Hub (only accessible if you're running Windows 10).

I've gone over the descriptions, stood on my head and squinted real hard, and I'm still left with the overwhelming feeling there's some core functionality, some higher purpose, that I just don't understand.

Clearly, Microsoft is trying to move us to a world where the Win10 upgrade is no longer free -- where, for example, entering a Win7 activation key won't activate Win10. We're facing a licensing maze straight out of Byzantium.

Based on the documentation we have so far, it looks like "genuine" copies of Windows 10 will have a digital license. (Eight months ago, Microsoft coined the term "digital entitlement," and apparently a digital license is the same thing.)  If you upgrade a genuine copy of Win7 or 8.1 to Win10 prior to July 29, 2016, there's a digital license stored on Microsoft's servers that says "this PC is licensed to use Win10." If you buy a new PC with Windows 10 pre-installed, there's a similar digital license on Microsoft's servers. Apparently, if you actually bought Windows 10 (there must be a dozen people who have), there's also an analogous digital license. Fair enough. Those have been the rules of the game for almost a year.

But those rules don't work very well when, for example, you upgrade your PC's motherboard, or if you accidentally install Win10 Home on a system that has a license for Pro and then try to revert to Pro. We've had problems with those outlying situations for decades. They've invariably been resolved by phoning the Microsoft activation center and asking for a stay of execution.

In all cases, the licenses have ultimately been assigned to one, single machine. One PC, one license. (Again, I'm not talking about Enterprise versions.)

Now a third variable has been added to the equation: the Microsoft account. Having been through the Activation Troubleshooter descriptions backward and forward, it's not clear to me how the bilateral status quo (one PC = one license) will shift to a trilateral PC --> license --> customer account triangle.

In simple situations, there will be no problem. When you sign in to an activated PC using a Windows account, the account will automatically pick up on the license. The Insider Hub article goes into great detail on how to manually link a Microsoft account to a specific license. (Hint: you have to do it while running the licensed machine.) If your PC suddenly becomes "ungenuine" -- the example given involves a "hardware change," which presumably includes changing the motherboard -- you can use your Microsoft account to re-establish the license-PC link and make your modified hardware "genuine" once again.

That's all well and good in normal circumstances. The procedure merely underlines the fact that Windows licensing has shortcomings. It always has.

At the same time, though, it introduces more questions than it solves. Kludges often do.

The fundamental question: Does the Microsoft account own the license? If so, the owner should be able to move the license from PC to PC, burning the old license in its wake. If not, what happens when, for example, the genuine machine is sold to someone else? Does the license move with that system, or does the license go with the owner's Microsoft account?

There are many more questions. Anybody's who's suffered through a graph theory class could have a field day. 

I'm all for simpler licensing. Unfortunately, the Activation Troubleshooter technique takes the potential for licensing screw-ups into an entirely new dimension.

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