This entry isn't really VMware-specific and actually falls along the lines of an activity I have to perform occasionally and always forget the finer details of. I'm posting the steps here for me, but hopefully they will help others as well. Sometimes there is a need to change the edition of Windows. For example, to leverage those 32 vCPUs in virtual machine hardware version 8, Windows Standard won't work. Applications and their requirements grow, and it can be very useful to upgrade Windows editions in a simple and non-disruptive way.

 

Windows Server 2008 R2 contains a command-line utility called DISM (Deployment Image Servicing and Management tool). This tool has many features, but one of those features is the ability to upgrade the edition of Windows in use. Note that this process is for upgrades only and is irreversible. 

 

To get started, issue the following command to determine the current edition:

DISM /online /Get-CurrentEdition

 

Note the edition and then issue the following command to determine the edition upgrade options:

DISM /online /Get-TargetEditions

 

Now that we know what we have and what the upgrade options are, there is only a single command left to perform the edition upgrade. This is also the tricky part of this process and the part that I basically created this entry for.

 

Once ready to change editions, issue the following command:

DISM /online /Set-Edition:<edition ID> /ProductKey:XXXXX-XXXXX-XXXXX-XXXXX-XXXXX

 

The <edition ID> field is the version information obtained in step 2. For example, ServerEnterprise or ServerDatacenter. The ProductKey field needs to be one of the KMS Client Setup Keys listed at  http://technet.microsoft.com/en-us/library/ff793421.aspx. This is the step that always gets me, as I want to just use a real KMS key that I control. These real KMS keys will not work for this step. Use the appropriate KMS Client Setup Key for the edition of Windows that was specified in the <edition ID> field. For example, if ServerEnterprise was used, then use the KMS Client Setup Key for Windows Server 2008 R2 Enterprise. For example, to upgrade Windows Server 2008 R2 Standard editionn to the Enterprise edition:

DISM /online /Set-Edition:ServerEnterprise /ProductKey:489J6-VHDMP-X63PK-3K798-CPX3Y

 

Shortly after this command is entered, follow the reboot prompts. Once the rebooting is complete, log back in to Windows and use the Activation Wizard to change the product key to your valid KMS key and activate the upgraded version of Windows.

 

Most of the content from this entry, along with a few important caveats, can be found at:

http://blogs.technet.com/b/server_core/archive/2009/10/14/upgrading-windows-server-2008-r2-without-media.aspx

 

Thanks for reading,

Brian