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Windows Server 2008 R2 Upgrade Paths

Let me start by saying that I am definitely not a fan of “in-place” upgrades. However, there are scenarios where you simply must choose this option. Before summarizing what is supported, it’s a good idea to go over what is not supported.

Unsupported Upgrade Scenarios

  • Windows 9x, Windows Millennium, Windows XP, Windows Vista Editions, or Windows 7
  • Windows NT Server 4.0
  • Windows 2000 Server
  • Windows Server 2003 (RTM & SP1), Windows Server 2003 Web
  • Windows Server 2003 for Itanium-based Systems
  • Windows Server 2008 R2 (M3 or Beta)
  • Windows Server 2008/2008 R2 for Itanium-based Systems
  • Cross-architecture in-place upgrades (x86 –> x64)
  • Cross-language in-place upgrades
  • Cross-edition upgrades (Foundation –> Datacenter)
  • Cross-build type in-place upgrades

Supported Upgrade Scenarios

From Server 2003 (SP2, R2) –> Server 2008 R2

  • Standard –> Standard, Enterprise
  • Enterprise –> Enterprise, Datacenter
  • Datacenter –> Datacenter

From Server 2008 (SP1, SP2) –> Server 2008 R2

  • Web –> Web, Standard
  • Web Core –> Web Core, Standard Core
  • Standard –> Standard, Enterprise
  • Standard Core –> Standard Core, Enterprise Core
  • Enterprise –> Enterprise, Datacenter
  • Enterprise Core –> Enterprise Core, Datacenter Core
  • Datacenter –> Datacenter
  • Datacenter Core –> Datacenter Core

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