There are a number of supported and unsupported ways to upgrade to either Windows 7 or Windows Server 2008 R2 and knowing exactly what is supported will ensure you and your clients aren't placed into a compromising situation. So, have a read of the following 2 documents to get the skinny on the situation:
Windows 7 Upgrade Paths
Windows Server 2008 R2 Upgrade Paths
Basically, when it comes to Windows 7, upgrading directly from Windows XP (or earlier) is unsupported whereas upgrading from Windows Vista to the equivalent or better version of Windows 7 is supported (ie upgrading from Windows Vista Business to Windows 7 Professional, Ultimate or Enterprise is supported).
To be honest, we don't ever upgrade desktop operating systems as the time involved and the result often isn't what we'd like - we perform a fresh install of the OS, drivers and applications.
With Windows Server 2008 R2, upgrades are supported from Windows Server 2003 SP2 or R2 or from Windows Server 2008 RTM-SP1 or SP2 and from nothing else.
Regards,
The Outspoken Wookie
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