Is it unwise to jump two Windows Server versions?

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Windows Server 2008
Windows Server 2012
We've been running an ASP.NET website on Windows Server 2003 but now we're looking to move it to a new server on a more recent operating system. Should we jump from 2003 to 2012 or should we just start with 2008?

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I’d go straight to Windows Server 2012 R2. Windows 2008 is going to be out of support soon (if it isn’t already) so moving stuff to that OS isn’t the best idea. I’d go as current as possible so that when you don’t want to upgrade for another 10 years you aren’t 14 years behind the ball. Also in a few years finding people willing to / know how to support Windows 2008 will start getting harder as everyone wants to support the newer stuff.

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  • jinteik
    to me windows 2008 is good enough to run most of the stuff today, but maybe you would like to play around with windows 2012 before deciding which is the best for you
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  • carlosdl
    Agreed.

    You will probably want to update your website to use a newer version of the .NET framework too, so, it would be wise to go straight to 2012 R2 as Denny suggested.
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  • excellentrandy
    Better to play around first with Windows Server 2008 and 2012. Then, it's up to you to decide which OS is more user friendly and you will never have a hard time in using. 
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  • mrgeek1974
    Personally I think you can be brave to go to W2012 in one move. I can't imagine what extra problems will be expected, but imagine with ease the pack of troubles involuntarily evolved when you try to move to one OS and then to the second OS in a short time.
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