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With Visual Studio 2010 right around the corner, what does Visual Studio 2008 Professional with MSDN Professional upgrade to in Visual Studio 2010? Do I get 2010 for free, if I buy this flavor of 2008 now?
If your subscription is still active when Visual Studio 2010 is released, then yes, you will be able to download Visual Studio 2010.
Microsoft has changed the MSDN licensing a bit; the “Visual Studio 2008 Professional with MSDN Professional” will just be called “Visual Studio 2010 Professional with MSDN.”
There’s a press release from Microsoft explaining the changes (MS Word Link).