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Supported paths for upgrading from Windows Server 2003 to Windows Server 2008

In case you're considering an upgrade, Microsoft recently released KB951041 which discusses the supported ways to complete an upgrade. Note here that it is my personal opinion that upgrades should be only a stopgap measure until you can complete a full rebuild on any server. You flush out all your prior mistakes that way...

From the knowledgebase article:

From Windows Server 2003 Standard Edition Service Pack 2 (SP2) or from Windows Server 2003 Standard Edition Service Pack 1 (SP1), you can upgrade to the following versions of Windows Server 2008:


  • Windows Server 2008 Standard

  • Windows Server 2008 Enterprise

  • Windows Server 2008 Standard without Hyper-V

  • Windows Server 2008 Enterprise without Hyper-V

From Windows Server 2003 Enterprise Edition SP2 or from Windows Server 2003 Enterprise Edition SP1, you can upgrade to the following versions of Windows Server 2008:


  • Windows Server 2008 Enterprise

  • Windows Server 2008 Enterprise without Hyper-V

From Windows Server 2003 Datacenter Edition SP2 or from Windows Server 2003 Datacenter Edition SP1, you can upgrade to the following versions of Windows Server 2008:


  • Windows Server 2008 Datacenter

  • Windows Server 2008 Datacenter without Hyper-V

From Windows Server 2003 R2 Standard Edition SP2 or from Windows Server 2003 R2 Standard Edition SP1, you can upgrade to the following versions of Windows Server 2008:


  • Windows Server 2008 Standard

  • Windows Server 2008 Enterprise

  • Windows Server 2008 Standard without Hyper-V

  • Windows Server 2008 Enterprise without Hyper-V

From Windows Server 2003 R2 Enterprise Edition SP2 or from Windows Server 2003 R2 Enterprise Edition SP1, you can upgrade to the following versions of Windows Server 2008:


  • Windows Server 2008 Enterprise

  • Windows Server 2008 Enterprise without Hyper-V

From Windows Server 2003 R2 Datacenter Edition SP2 or from Windows Server 2003 R2 Datacenter Edition SP1, you can upgrade to the following versions of Windows Server 2008:


  • Windows Server 2008 Datacenter

  • Windows Server 2008 Datacenter without Hyper-V

From the following versions of Windows Server 2003, there are no supported upgrades:


  • Windows Server 2003 Web Server Edition SP2 and Windows Server 2003 Web Server SP1

  • Windows Server 2003, Enterprise Edition for Itanium-based Systems

  • Windows Compute Cluster Server 2003

Read past the fold for some special considerations for Server Core and a few additional notes.

Upgrade considerations for Server Core installations of Windows Server 2008


  • You can use the Server Core installation option only by performing a clean installation.

  • You cannot upgrade from earlier versions of Windows to Server Core installations of Windows Server 2008.

  • You cannot upgrade from non-Server Core installations of Windows Server 2008 to Server Core installations of Windows Server 2008.

  • You cannot convert Server Core installations of Windows Server 2008 to non-Server Core installations of Windows Server 2008.

  • You can upgrade Server Core installations of Windows Server 2008 only to Windows Server Core R2 when it is released.

Additional notes


  • Upgrades can be performed only between versions of Windows that share the same architecture, such as x86 to x86, x64 to x64, or IA-64 to IA-64. For example, you cannot upgrade x86 versions of Windows to x64 versions.

  • You must have Windows Server 2003 SP2 or Windows Server 2003 SP1 installed to upgrade to Windows Server 2008. You cannot upgrade to Windows Server 2008 from the release version of Windows Server 2003.

  • You cannot upgrade to Windows Server 2008 from a Windows Server 2003-based computer that is running the Cluster service. For more information, click the following article number to view the article in the Microsoft Knowledge Base:

  • 935197 (http://support.microsoft.com/kb/935197/) You cannot upgrade the operating system of a clustered server from Windows Server 2003 to Windows Server 2008

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Posted by Greg Shields on May 8, 2008 12:30 AM |

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Greg Shields' Bio:

Greg Shields, is an independent author, instructor, and IT consultant based in Denver, Colorado, and a co-founder of Concentrated Technology. With nearly 15 years of experience in information technology, Greg has developed extensive experience in systems administration, engineering, and architecture specializing in Microsoft systems management, remote application, and virtualization technologies. Greg is a Contributing Editor for Redmond Magazine, MCPmag.com, and Virtualization Review Magazine and is the author of five books, including Windows Server 2008:  What’s New / What’s Changed. Greg is also a highly sought-after instructor and speaker, speaking regularly at conferences like TechMentor Events, and producing computer-based training curriculum for CBT Nuggets.  Greg is a recipient of Microsoft "Most Valuable Professional" award with a specialization in Windows Terminal Services.