Well just because I'm an obsessive programmer, who can't stand it when a module's code works, and mine don't, I finally got my manual version to work by closely examining the module's methods. :-) Use the module, it's way better. This just demonstrates how to waste half an hour of eye strain. :-)

#!/usr/bin/perl
use warnings;
use strict;
use Net::SMTP::SSL;                                                   
+              

my $user = 'me@gmail.com';
my $pass = 'foobarbaz';

my $server     = 'smtp.gmail.com';
my $to         = 'me@gmail.com';
my $from_email = 'me@gmail.com';
my $subject    = 'smtp-ssl-auth test';

my $smtps = Net::SMTP::SSL->new($server, 
                               Port => 465,
                               DEBUG => 1,
                               ) or warn "$!\n"; 

# authenticate
defined ($smtps->auth($user, $pass))
    or die "Can't authenticate: $!\n";

# send preliminary data
$smtps->mail("$from_email\n");
$smtps->to("$to\n");
$smtps->data();

#send header
$smtps->datasend("From: $user\n");
$smtps->datasend("To: $to\n");
$smtps->datasend("Subject: $subject\n");
$smtps->datasend("Reply-To: $from_email\n");
$smtps->datasend("MIME-Version: 1.0\n");
$smtps->datasend("Content-Type: text/plain\n");
$smtps->datasend("\n");
#send text body
$smtps->datasend("This will be the body of the message.\n");
$smtps->datasend("\n--\nVery Official Looking .sig here\n");
$smtps->datasend("\n");
$smtps->dataend();

print "done\n";
[download]

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