Let me start by saying that I am definitely not a fan of "in-place" upgrades. However, there are scenarios that you simply must choose this option. Before summarizing what is supported, its 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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