Here is a simple script. It works with my local ISP, but GMAIL smtp seems to reject it, and that is not Perl's fault.

Update: It seems if you send a test.doc , instead of .zip, GMAIL's smtp will accept it. Apparently to avoid viruses for windows users, they block .zip and .exe attachments. ???

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

my $user = 'zentara@woohoo.org';
my $pass = 'whatdoyouguess';

#$server     = 'your-smtp-server';
my $server     = 'smtp.woohoo.com';
my $to         = 'user@some.net';
my $from_name  = 'zentara';
my $from_email = 'zentara@woohoo.org';
my $subject    = 'smtp-ssl-auth test attach';

my $msg = MIME::Lite->new(
From     => $from_email,
To       => $to,
Subject  =>'test message',
Type     =>'TEXT',
Data     =>'This is a test, i repeat only a test',
);

$msg->attach(Type   =>'application/octet-stream',
Encoding =>'base64',
Path     =>'./test.zip',  #full path
);

#    Type     => 'application/msexcel',
#    Path     => $report,
#    Filename => 'college_orders.xls',
#    Encoding => 'base64'


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

# this works in early 2010
defined ($smtps->auth($user, $pass))
    or die "Can't authenticate: $!\n";


$smtps->mail($from_email);
$smtps->to( $to );
$smtps->data();
$smtps->datasend( $msg->as_string() );
$smtps->dataend();
$smtps->quit();

print "done\n";
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