Is it possible to upgrade Windows Server 2012 to Server 2012 R2 when Native VHD Boot is used? So far I have found it's not possible. I've looked through the DISM documentation and it mentions offline updated, but I do believe that refers to OS patching, not direct upgrades. If this isn't possible, why not? I would imagine folks would rather upgrade an OS than deploy new for things like Domain Controllers, infrastructure servers, or even client OS like Windows 8 to Windows 8.1.