For some organizations who purchased Microsoft 365 E3 or E5 licenses with corporate Windows device embedded with Windows 10/11 Pro license they can easily upgrade to Windows 11 Enterprise – this is called Windows Subscription Activation feature. It was first introduced with Windows 10 to allow device with Windows Pro edition to upgrade to Enterprise edition or Windows Pro Education to Windows Education edition. This feature does not requires human intervention for the most of time as long as the user’s AAD account have E3 or E5 license assigned, however, recently I do encountered a strange issue where I was trying to perform an upgrade from Windows 10 to Windows 11 on several devices.
The issue is that the Windows 10 device (Windows 10 Enterprise) plus the AAD account are all good, but after performed an in-place upgrade to Windows 11 which the license was being downgraded from Enterprise to Pro edition without error message.
But after I perform an investigation I spot an error displayed on the activation page from the Setting app that shows “Please sign in to your work or school account to verify your information”.
Here I’m sharing my troubleshooting process which resolved this issue:
1.Trying to click the “Sign in” button to sign in with one of the AAD account > then checking the license status with the Settings app. Nothing changed even performed with a reboot.
2.Then I was performing a manual activation with “slmgr /ato” command, no errors with reboot performed still the same.
3.So, I think should checking the device status to see whether the device able to sync policies pushed by MDM as the device is AAD joined > then I do spot an error under the “Device sync status” section > so perform the manual sync > successfully.
4.Heading back to the Setting app > System > Activation > perform sign-in action displayed on top of “Activation state” > successfully. The device license was upgraded from Pro edition to Enterprise without error.
Conclusion
Whenever encounter such activation issue or similar one, remember that Subscription Activation works requires device possesses Win10/11 Pro license + AAD account with E3/E5 license assigned. As long as the condition are meet the issue probably caused due to lack of authentication.
