Doesn't matter if it is on Win32 or *nix, I could not build Email::Stuff onWin32, so I tried it on one of my CentOS testing servers:

#!/usr/bin/perl
use warnings;
use strict;
use Email::Stuff;
my  $objst = Email::Stuff
        ->to('jophnday@wordsnimages.com')
        ->from('praecipuus@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 => 'praecipuus',
        password => 'xx***xx',
        Debug    => 1,
    );
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Result:

Name "IO::Socket::SSL::DEBUG" used only once: possible typo at emailst
+uff.pl line 13.
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 /usr/lib/perl5/site_perl/5.8.7/Email/Send/SMTP.pm line 37
[download]

jdtoronto