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The newest Mac OSX version of the Mono (2.10.10) doesn't include the VisualBasic.dll (and I'm assuming other files that go along with this). VB.net applications that function perfectly fine with Mono version 2.10.9 no longer work with version 2.10.10. Things like Ctype are breaking because the application cannot locate the VB dlls. This is the first time I've entered a bug so if there is something else you need from me, let me know.
My testing was done on OSX
Duncan, I believe this is your area.
This works with recent mono versions.