Issues Upgrading Windows 10 Pro to Enterprise with AzureAD and E5 Licenses

A client of ours wanted to upgrade their Windows 10 Professional licenses to Windows 10 Enterprise by way of E5 licensing in Office365 / Azure Active Directory.

Most computers worked fine, but a few just didn’t work and upgrade as they should have. There isn’t a lot of documentation on this, so I thought I’d put out there what worked for us and what we found. I ended up opening a ticket with Microsoft Escalated Support and worked with a rep over a few weeks.

First and foremost, make sure in Office365 that the E5 license has the option checked off for Windows 10 Enterprise.

First Troubleshooting Recommendation: dsregcmd

Run dsregcmd /status on the affected machine as the logged in user (and not a System or admin account).

If WamDefaultSet : ERROR and / or AzureAdPrt : NO are found, these would indicate an issue on Azure’s end. You want to see both answered with YES. These fields indicate whether the user has successfully authenticated to Azure AD when signing in to the device.

If the values are NO, it could be due to:

  • Bad storage key in the TPM associated with the device upon registration (check the KeySignTest while running elevated).
  • Alternate Login ID
  • HTTP Proxy not found

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