> C:\>ruby -ve 'p File.expand_path("~")'
> ruby 1.9.1p0 (2009-01-30 revision 21907) [i386-mswin32]
> "C:/Documents and Settings/phasis"

Odd:

D:\dev>c:ruby -ve 'p File.expand_path("~")'
ruby 1.9.1p129 (2009-05-12 revision 23412) [i386-mingw32]
"/Documents and Settings/Melissa.BLACKY"

maybe I should try p0 again :)
My guess is it's some compiler define not set right.
-=r
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