..just a shot in the dark here, but what if you split up the eval into 2?

BEGIN 
{
    eval{
        require Expect;
        import Expect;
    };
    eval{
        require Win32::Setupsup;
        import Win32::Setupsup;
    }
}
[download]

I think when windows fails to require Expect, it's bailing from the eval and not getting to the require Win32 stuff..

update: hmmm.. ++broquaint