I personally use Net::SMTP::SSL; for Gmail on a Win32 system

You did not mention it in your post so I thought I'd throw it out there. That is the module that has been working for me through Gmail. I don't recall if I had to add any additional repositories, but I *do* know I installed it via PPM without headache.

If you can get that installed, check the examples or I can post a simple bit of code to help with sending a message. I don't immediately think the code will help though since your trouble seems to be with getting a proper module loaded in windows anyway...

This issue has come up a few times see Using MIME::Lite with TLS or use super search to find more threads on this subject. Perhaps you need to set up more PPM repositories or simply use cpan, which has shipped with AS perl for some time now.

Type c:\ppm install mingw from the command prompt to download a compiler and build tools required to use cpan compiling c/c++ modules or see A guide to installing modules for Win32 regarding setting up more repositories.

Update: note the strike out.

Done (but I think that isn't exactly a "really simple solution")!
I have to add this repository: http://cpan.uwinnipeg.ca/PPMPackages/10xx/

Then I have to install:
Net-SMTP-SSL
Net-SMTP-TSL
Net-SSLeay
IO-Socket-SSL


This code works:

use strict;
use warnings;

use FindBin;
use Net::SMTP::TLS;  
use MIME::Lite;

use lib ("$FindBin::Bin/CPAN");

my $msg = MIME::Lite->new(
        From    => 'me@gmail.com',
        To      => 'you@gmail.com',
        
        Subject => 'A message with 2 parts...',
        Type    => 'multipart/mixed',
);
    
#$msg->attach(
#    Type     => 'TEXT',
#    Data     => "Here's the GIF file you wanted",
#);

#    $msg->attach(
#        Type     => 'plain/txt',
#        Path     => 'Log/output.log',
#        Filename => 'output.log',
#    );


my $mailer = new Net::SMTP::TLS(  
    'smtp.gmail.com',  
    Hello   =>      'smtp.gmail.com',  
    Port    =>      587,  
    User    =>      'me@gmail.com',  
    Password=>      'my-pwd');  
$mailer->mail('me@gmail.com');  
$mailer->to('you@gmail.com');  
$mailer->data;  
$mailer->datasend($msg->as_string);  
$mailer->dataend;  
$mailer->quit;
[download]




With this other code, until now, I have an authorization error (I don't know why):
---------------------------
UPDATE: Also the second code below works fine, but you need to install an extra package: Authen-SASL
So for the code above (TLS way), you need these packages:
Net-SMTP-SSL
Net-SSLeay
IO-Socket-SSL

For the code below (SSL way), you need these packages:
Net-SMTP-SSL
Net-SSLeay
IO-Socket-SSL
Authen-SASL

But any suggestion, in order to have a better code, is still welcome!

---------------------------

use Net::SMTP::SSL;

sub send_mail {
my $to = $_[0];
my $subject = $_[1];
my $body = $_[2];

my $from = 'me@gmail.com';
my $password = 'my_pwd';

my $smtp;

if (not $smtp = Net::SMTP::SSL->new('smtp.gmail.com',
                            Port => 465,
                            Debug => 1)) {
   die "Could not connect to server\n";
}

$smtp->auth($from, $password)
   || die "Authentication failed!\n";

$smtp->mail($from . "\n");
my @recepients = split(/,/, $to);
foreach my $recp (@recepients) {
    $smtp->to($recp . "\n");
}
$smtp->data();
$smtp->datasend("From: " . $from . "\n");
$smtp->datasend("To: " . $to . "\n");
$smtp->datasend("Subject: " . $subject . "\n");
$smtp->datasend("\n");
$smtp->datasend($body . "\n");
$smtp->dataend();
$smtp->quit;
}

# Send away!
&send_mail('you@gmail.com', 'Server just blew up', 'Some more detail')
+;
[download]

Any suggestion is welcome!

Don't set your HELO string to smtp.gmail.com. That will eventually (quickly?) get you put on a blacklist, which is annoying to get off. A HELO string is meant to be your hostname, not the hostname of the mail server you are connecting to. The mail server already knows what its hostname is ;)

And with your new, edited code, make sure you specify the HELO string. Net::SMTP uses 'localhost.localdomain' as the default HELO string, which will also get you blacklisted.

However, I'm not 100% sure if identifying yourself with SASL auth will protect you from being blacklisted, but it's better to be safe than sorry ;)

"Done (but I think that isn't exactly a "really simple solution")!"

Well it's a lot simpler than not using any of these modules/libraries and writing it all yourself :) Seriously though, which parts did you have difficulty with, installing the modules?