Server Core Anytime Upgrades

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ServerCore Windows Vista had a neat trick up its sleeve, that allowed admins to change the Vista SKU without the need for reinstallation or installation media. One could, for instance, 'transition' a Windows Vista Home Basic installation to Windows Vista Home Premium, Business, Ultimate or Enterprise. This functionality is called Windows Anytime Upgrade (WAU)

Windows 7 and Windows Server 2008 R2 also have this functionality built-in. (Unfortunately Windows Server 2008 does not.)

So, let’s look how Windows Anytime Upgrades work on Server Core installations of Windows Server 2008 R2.


Windows Anytime Upgrade FAQ

So let’s look at Anytime Upgrades a bit deeper:

Q: Is a Windows Anytime Upgrade the same as an In-place Upgrade?
A: No. In-place Upgrades can be performed to upgrade a previous version of Windows to a more recent version of Windows. Anytime Upgrades are only possible between the same version of Windows.

Q: Are Windows Anytime Upgrades possible between architectures, e.g. between x86 and x64?
A: No. Anytime Upgrades are only possible between SKUs of the same architecture.

Q: Do I need to download a Windows Update for Windows Anytime Upgrades?
A: No you don’t. The only network communication is for Windows activation.

Q: Can I revert back after a successful Windows Anytime Upgrade?
A: No, Windows Anytime Upgrades are one-way processes.

Q: Can I perform Windows Anytime Upgrades in Windows Server 2008?
A: No. This feature is not available in Windows Server 2008.

Q: How much time does a typical Windows Anytime Upgrade take?
A: Most of the time will be taken up by the two system restarts.The rest of the process would normally take a couple of (Microsoft) minutes.

Q: Can the server be a Domain Controller?
A: No, the server cannot be a Domain Controller or Certificate Authority at the time of Windows Anytime Upgrade.

Q: Can I use Windows Anytime Upgrade to change between (OEM, MAK, KMS) productkeys?
A: No, if you want to change the licensing channel, use the slmgr.vbs tool


Windows Anytime Upgrade paths

The first thing to look at is the Windows Anytime Upgrade paths available, based on the installed Windows Server SKU. The table below shows these paths for the available Server Core flavors of Windows Server 2008 R2:


Source Windows Server 2008 R2 SKU Target Windows Server 2008 R2 SKU
Windows Server 2008 R2 Standard x64
Windows Server 2008 R2 Enterprise x64
Windows Server 2008 R2 Datacenter x64
Windows Server 2008 R2 Enterprise x64
Windows Server 2008 R2 Datacenter x64


Windows Anytime Upgrade commands

To Anytime Upgrade a Server Core installation of Windows Server 2008 R2, use the following commands.

First, determine the SKU your Server Core installation is running. Use the following command:

dism.exe /online /Get-CurrentEdition

Then, you’re ready to check for possible target SKUs. Run:

dism.exe /online /Get-TargetEditions

Finally, to initiate an upgrade, run:

dism.exe /online /Set-Edition:Edition /ProductKey:ProductKey

Where Edition can be ServerDatacenter or ServerEnterprise and ProductKey is the 25-digit productkey, notated with dashes. For instance: ABCDE-FGHIJ-KLMNO-PQRST-UVWXY.


Windows Anytime Upgrade Benefits

After you perform a Windows Anytime Upgrade, you reap the following benefits:

  • Enterprise Edition and Datacenter Edition offer the Failover Clustering feature.
    When you’re looking to convert a Standard Edition installation into a cluster, however, the Anytime Upgrade feature is for you. Check, however, whether the application, role or feature can handle an Anytime Upgrade.
  • Enterprise Edition and Datacenter Edition offer more flexible ways to license virtual machines running on the installation. Standard Edition allows for one virtual licensed Windows installation. Enterprise Edition allows for up to four virtual licensed Windows Installations. Datacenter allows for unlimited virtual licensed Windows Installations.



Windows Anytime Upgrades can be useful for Windows Server installations to reap the benefits of an upscale SKU. For Server Core installations, these benefits aren’t really big.

One day, perhaps, the Anytime Upgrade functionality will be of major importance to Server Core installations. This might be the day when Anytime Upgrades can be used to switch from Server Core installations to Full installations and vice versa.

Related posts

Server Core Roles and Features in 2008 R2
Core flavors of Windows Server 2008

Further reading

Upgrading Windows Server 2008 R2 without media
Windows Anytime Upgrade: frequently asked questions
Upgrading Windows Server 2008

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