Linking Windows 10 licenses to Microsoft Accounts

Microsoft introduced a new feature in windows 10 Build 14371 that allows you to link the digital license of the operating system to a Microsoft Account.

Even though Microsoft stated in the announcement that the feature is available starting with Build 14371, things look different currently than how Microsoft describes them.

Considering that this is a preview build after all, you can expect the feature to become available with the Anniversary Update at the latest.

Microsoft describes the feature in the following way:

Based on Insider feedback, 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.

According to the announcement, Microsoft Accounts will be automatically linked to the license when used to sign in.

The Activation Troubleshooter is another new feature introduced in the same build. Basically, it allows you to run it to re-activate a system under certain circumstances. Microsoft mentions hardware changes but also when the wrong version of Windows is installed on the device.

Using the Activation Troubleshooter

1. The Activation Troubleshooter will be available in the Settings application under Update & Security > Activation. There you need to select the troubleshoot option to run it.
2. The Troubleshooter attempts to activate Windows and if that works, you are done and the operating system should be activated.
3. If that fails, it displays the message "We weren't able to activate Windows on this device".  A link to "I changed hardware on this device recently" is provided on the screen. Click on it to start the new activation process.
4. You have to enter your Microsoft Account username and password, and sign in to the account. You may also have to enter the local account password if you have not linked the Microsoft Account to the system.
5. From the list of devices that appear, select the device that you are currently using. Check "This is the device I'm using right now" and click on the activate button.

Activation questions

The process seems straightforward enough: sign in with a Microsoft Account, get the digital license linked to the account so that you can run the Activation Troubleshooter at a later point in time to fix activation issues without having to contact Microsoft.

Microsoft has a habit of revealing only some information, and this is one of those situations where an announcement raises more questions than it answers.

First of all, is the license linked to any Microsoft Account that signs in on a device? Or is the license only linked to the first Microsoft Account? If it is linked to every Microsoft Account, can you get multiple licenses assigned to a single account? Can you even collect them by signing in on devices with a Microsoft Account?

Second, does the linking to Microsoft Accounts remove the license link to the single PC? Can you install Windows 10 on another device after linking an upgraded copy of the operating system to a Microsoft Account, sign in with that account on the new device, and get it activated using the Activation Troubleshooter?

Or is the linking to the Microsoft Account used solely for reactivating the license on the same device? This would however require the linking of device information to the Microsoft Account.

Third, Microsoft mentions on the Feedback Hub that there is a reactivation limit, but fails to mention it. In the best case, this would mean that you cannot use the Activation Troubleshooter to activate the copy of Windows 10 on the device, and that you would need to contact Microsoft for that.

Fourth, does the linking of the license to a Microsoft Account affect selling the device or handing it over to someone else? Can you remove the link between a license and a Microsoft Account? Can you reactivate a new device with that license after selling an activated PC?