Indeed, Email::Stuff is just a usability wrapper (I wrote it that way intentionally).
Trouble with IO::Socket::(Anything) on Win32 would not surprise me at all, there's a few dragons there.
What Perl distribution are you using?
The first step might be to just write a simple test script that tries to connect via SSL, then immediately drops the connect once established, to GMail's server and see if that works.
That would isolate the problem to the connectivity layer. If you can get that working, then lets look at Email::Stuff and friends.
Until then though, I consider the entire Email:: family to be blameless here.
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