Well I'm not doing any better than you, although being on Win32 may distort things. Got some error messages though...

I ended up spliting up the call string in order to intervene in the setup steps:

my  $objst = Email::Stuff
        ->to('tshinnic@io.com')
        ->from('tshinnic@gmail.com')
        ->subject('Test Subject')
        ->text_body('This is a test.');
# This forces Net::SMTP::SSL to be loaded
    $objst->using( 'SMTP', ssl => 1 );
# Which allows us to do this ...
    $IO::Socket::SSL::DEBUG = 1;
my  $rc = $objst->send('SMTP',
        ssl      => 1,
        Host     => 'smtp.gmail.com',
        PeerPort => 465,
        username => 'tshinnic',
        password => 'xxx',
        Debug    => 1,
    );
[download]

which finally gets us an actual error message!

CA file certs/my-ca.pem not found, using CA path instead.
IO::Socket::INET configuration failederror:00000000:lib(0):func(0):rea
+son(0)
 at C:/Perl587/site/lib/Email/Send/SMTP.pm line 37
[download]

which is of very little help to me, anyway...

After taking the same extraordinary measures, what error messages do you see?

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