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Perhaps it's too similar to Windows 95 and 98?

This actually could be it. Too much legacy code that checks for "Windows 9*".

This hypothesis is supported by this redditor's comment, who is apparently an MS dev: http://www.reddit.com/r/technology/comments/2hwlrk/new_windo...

Also supported by this code search, which turns up a few classes in the JDK using this sort of check: http://www.reddit.com/r/programming/comments/2i14ny/if_osnam...

If they're skipping why not just fast forward to Windows 2014 (or 15).

That would keep up with SQL Server 2014 and Visual Studio, etc.