In-place upgrade of Windows Server 2008 R2 Standard to Enterprise

Windows Server 2008 R2 Standard has a hardware limit of 32GB of RAM. The server I was working on required 48GB of RAM for an SAP application and only 32GB was actually usable. To resolve this issue required upgrading to Windows Server 2008 R2 Enterprise whose memory limit is 2TB. Upgrading meant following one of two choices:

  1. Rebuild the server from scratch
  2. Perform an in-place upgrade

Naturally I did not want to go through the pains of rebuilding the server from scratch so decided to go for option 2 (in-place upgrade). I googled how to perform an in-place upgrade of Windows Server 2008 R2 Standard to Enterprise and my search quickly yielded this excellent post by Richard Skinner.

The steps below are documented in Richard Skinner’s post, please see his post and all credit goes to him for it.

The Upgrade Process

Originally my version of Windows was Server 2008 R2:

20150624114514

1. We are going to be using the DISM tool to perform the upgrade. Run the command below to show our current OS version:

C:\>DISM /Online /Get-CurrentEdition

Deployment Image Servicing and Management tool
Version: 6.1.7600.16385

Image Version: 6.1.7600.16385

Current edition is:

Current Edition : ServerStandard

The operation completed successfully.

C:\>

2. To find out the OS versions we can upgrade to run:

C:\>DISM /Online /Get-TargetEditions

Deployment Image Servicing and Management tool
Version: 6.1.7600.16385

Image Version: 6.1.7600.16385

Editions that can be upgraded to:

Target Edition : ServerDataCenter
Target Edition : ServerEnterprise

The operation completed successfully.

C:\>

3. Even if your environment uses KMS for internal activations, you will need to perform the upgrade using a “temporary” product key. You can obtain these KMS client setup keys from this Microsoft link. I used the product key for Windows Server 2008 R2 Enterprise.

Perform the upgrade to Enterprise Edition by running:

C:\>DISM /Online /Set-Edition:ServerEnterprise /ProductKey:XX
XXX-XXXXX-XXXXX-XXXXX-XXXXX

Deployment Image Servicing and Management tool
Version: 6.1.7600.16385

Image Version: 6.1.7600.16385

Starting to update components...
Starting to install product key...
Finished installing product key.

Removing package Microsoft-Windows-ServerStandardEdition~31bf3856ad364e35~amd64~
~6.1.7601.17514
[==========================100.0%==========================]
Finished updating components.

Starting to apply edition-specific settings...
Restart Windows to complete this operation.
Do you want to restart the computer now (Y/N)?Y 

Replace XX XXX-XXXXX-XXXXX-XXXXX-XXXXX with the relevant key from the Microsft link stated earlier.

4. Reboot the server and you will see that the version is now Windows Server 2008 R2 Enterprise:

20150624114105

5. The last step was to re-activate the server using a legitimate product key. The environment I was working on was using standard MAK activation so I just entered the actual product key and then re-activated it via the GUI. If you prefer re-activating via the command line follow the steps below:

Install your product key:

slmgr.vbs /ipk XXXXX-XXXXX-XXXXX-XXXXX-XXXXX

Activate the product key:

slmgr.vbs /ato

All done. Assuming your product key is legit :) your system should be activated.

The Happy Ending?

Hopefully the steps above worked for you. The upgrade steps worked for me although I encountered one issue – I was unable to RDP to the server. A bit of digging around found that the Remote Desktop section was missing from the Remote Tab. To fix this issue, follow the steps in this link.

Reference(s):
In Place Upgrade Of Windows Server 2008 R2 Standard To Enterprise Or Datacenter Edition
Physical Memory Limits: Windows Server 2008 R2
Deployment Image Servicing and Management Technical Reference