has anyone already upgraded successfully from Windows Server 2008 SP2 (64bit) to Windows Server 2008 R2 by using the Windows Anytime Upgrade?

According to some articles on the web, this should be a painless process by simply selecting the "Upgrade" option during the installation process.

However, I still have some questions:

  1. Will all the current software settings really be kept and still be working after the upgrade or might there be any issues, especially with software currently installed in the "Program Files (x86)" folder?
  2. Is there any rollback option in case the upgrade fails (except for making a full backup before and recover it afterwards, of course)?
  3. Can I perform the upgrade on my dedicated server with only Remote Desktop available or will this service be interrupted during the upgrade process?
  4. Will all my current sites, application pools and other webserver (IIS) settings be kept or will I have to reconfigure them entirely after the upgrade?

Sorry for asking such basic questions but I never did such an upgrade before and I just want to make sure that everything will be working as expected before considering this step.

Thank you very much in advance!

  1. Yes
  2. No, but you can make a good backup with windows backup inside 2008
  3. No, you need local access, IP KVM is enough
  4. Yes, will keep

You can look here and read more about upgrading: http://technet.microsoft.com/en-us/library/ff968983(v=WS.10).aspx

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    I have done this install over RDP before. You start the installer in windows and you will stay connected till the server reboots. Once the install is done you will be able to connect again via RDP. – evolvd Jul 12 '11 at 20:42

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