Jul 06, 2015

What would make a port from Server 2003 to 2008 or 2012 more complicated?

The dependencies of the app. If it is entirely self-contained, or only calls its own libraries, then you should be able to port it right over. But if your app makes extensive kernel calls, makes heavy use of the .Net libraries, or touches non-Windows servers in some way, then you will have more work to do. The kernel obviously changed between Server 2003 and 2008, and even moreso to 2012, and Microsoft tends to make big updates to the .Net framework, so what worked under one version may not work on another.
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