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I would like to know if I migrate from Windows Server 2003 to Windows Server 2008 (x64) do I have to reinstall all applications in new Operating System or I will be able to simply upgrade the OS without any data loss.

A: 

Check out this MS Technet Forum thread.

Windows Server 2003 and Windows Server 2003 R2 can both be upgraded in-place to Windows Server 2008, as long as you keep the following in mind:

  • The Windows Server 2003 patchlevel should be at least Service Pack 1
  • You can't upgrade across architectures (x86, x64 & Itanium)
  • Standard Edition can be upgraded to both Standard and Enterprise Edition
    • Enterprise Edition can be upgraded to Enterprise Edition only
    • Datacenter Edition can be upgraded to Datacenter Edition only

This might be your preferred option when:

  • Your Active Directory Domain Controllers can still last three to five years economically and technically)

  • You worked hard to get your Active Directory in the shape it's in.

  • Your servers are in tip-top shape.

Pekka

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