Azure – In-Place Upgrade Windows 2012R2 to Windows 2019

This method is not supported by Microsoft, but it is working well and allows you to Upgrade Windows 2012R2 to Windows 2019, here is step by step.

  1. Disable BitLocker (Suspend-BitLocker -MountPoint “C:” -RebootCount 0) if enabled of course.
  2. Download Windows Server 2019 – e.g. from https://my.visualstudio.com/Downloads?q=Windows%20Server%202012%20R2&pgroup=.
  3. Unzip .iso file using 7-zip.
  4. Run command prompt as a administrator and change directory to unziped .iso with Windows Server2019.
  5. Run command:

setup.exe /auto upgrade /DynamicUpdate enable /pkey WMDGN-G9PQG-XVVXX-R3X43-63DFG /showoobe none

and follow installer.

Btw. You noticed that Azure uses KMS for Activating Windows – here semoe more keys: https://docs.microsoft.com/en-us/previous-versions/windows/it-pro/windows-server-2012-r2-and-2012/jj612867(v=ws.11)

And enable BitLocker again via GUI (right clink on disk).