I wanted to ask if there a good reason to do a clean install of Windows Server 2012 and redo my configurations (a lot of hassel and hours of work) or just go with the straight upgrade of my Windows Server 2008 R2 machine. Are there any pitfalls or limitations anyone has encountered I should be aware of? Please advice.
closed as not constructive by SvW, Bryan, Michael Hampton♦, Ward, jscott Dec 13 '12 at 3:28
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Most people that perform clean installs have good reasons for doing so. Over the years, issues can develop, and starting with a known good configuration is one way to leave issues behind. It also facilitates a much quicker final cutover during transition of roles.
Turning up a replacement server with a clean install and moving the role(s) over to that server is very common in large organizations. The only time in recent memory when we performed an in-place upgrade was to replace standard edition with enterprise because the server was setup with an incorrect image, and we did not have time to re-provision.
Small businesses with limited resources may not have a separate server to move to, or the time, expertise and documented configuration to perform this type of clean transition.
The main caveat you may encounter is if the upgrade goes sideways, and you cannot resolve the issues, do you have a functional backout? That typically means restoring at a minimum the System/boot partition and System State. If you have not done that or are uneasy about it, the risk exposure of an in-place upgrade is very high. One way to mitigate that risk is to P2V the server to a VM, and attempt to perform the in-place upgrade there before attempting the upgrade on the real server, and also test the backup restore of the System partition and System State on the VM. Another risk mitigation may be to perform a local backup to a reasonably fast USB hard drive just before the upgrade. That usually facilitates the quickest possible restore.