Windows 2000 Server hardware may not be able to support Windows 2008. Assuming a particular server does meet the requirements for 2008, upgrading Windows 2000 to 2008 or R2 is a two step process: Upgrading from Windows 2000 Server to Windows 2003 SP2 and then to Windows 2008. Given the scope of changes between Windows 2000 Server and Windows Server 2008 such an upgrade process is not recommended. (Because Windows Server 2008 R2 is 64-bit only, it is not possible to upgrade from Windows 2000 Server to Windows Server 2008 R2 – even “through” Windows Server 2003.)
In terms of migrating a workload from an older server to a newer server running Windows Server 2008 or R2, in some cases it may be possible to migrate, easing the transition by preserving settings and configuration. Because server roles were introduced after Windows 2000 Server – and given the scope of changes and enhancements to server capabilities over the past 10 years – such a migration path would also, in many cases, involve moving first to Windows Server 2003 and then to Windows Server 2008 or R2.
Given the complications – whether upgrading or migrating – of attempting to move “through” Windows Server 2003 on the way to 2008 or R2 in these scenarios, they are not recommended. A clean install of Windows Server 2008 or R2 – typically on new server hardware is generally recommended.
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