Just for posteriority, MIME::Lite 3.031 now supports SSL directly:

MIME::Lite->send('smtp','some.host', SSL => 1, Port => 465 );
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Hello,

I have just finished my struggle (successful :))with MIME::Lite and SSL. I was using ActivePerl on Windows. Here are my observations:

1. Make sure that you have the most recent version of perl and all libraries - in most cases new versions of security related libraries are issued in order to fix bugs and compensate detected weaknesses, not to provide new bells and whistles. Therefore, backward compatibility is not the highest priority. Thus, if you have installed perl 3-4 years ago, uninstall it and get the newest version from ActiveState (or whatever distro you use)

2. MIME::Lite as it is right now DOES NOT support SSL. Or at least there is no clear simple way to make it work. With all that said, it IS POSSIBLE to make it work, but you have to modify the library code. But the hack is simple: In the MIME/Lite.pm file find a definition of @_net_smtp_opts table and make sure that it looks like this:

my @_net_smtp_opts = qw( Hello LocalAddr LocalPort Timeout AuthUser
                         AuthPass SSL
                         Port ExactAddresses Debug );
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Explanation: MIME::Lite uses Net::SMTP for SMTP protocol. However, for some reason it does not pass all arguments of MIME::Lite->send* method to Net::SMTP->new. It filters them by @_net_smtp_opts table. Only parameters which are in this table are being passed to Net::SMTP constructor. Originally SSL, AuthPass, AuthUser are not there. That's why they never make it to Net::SMTP module.

MIME::List->send('smtp', $host, AuthUser=>$user, AuthPass=>$pass, Port
+=>465);
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 Unexpected EOF on command channel at c:/Perl/site/lib/MIME/Lite.pm li
+ne 2865
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If your providers server listens on port 465 (as indicated in the code snippet above), it almost certainly expects an SSL connection (465 is the universally accepted port for SMTPS,i.e. SMTP over SSL). AFAIK you can't use SSL in conjunction with the MIME::Lite send() method (or rather, you probably could but it's more trouble than it is worth), so you'll need to use something like Net::SMTP::SSL for sending. You can still use MIME::Lite for constructing the message. For example (untested):

#!/usr/bin/perl

use strict; 
use warnings; 
use MIME::Lite::TT::HTML; 
use Net::SMTP::SSL;

my %params;
my %options; 
$options{INCLUDE_PATH} = 'c:/Documents and Settings/Uriel/My Documents
+/Sandbox/perl/'; 

my $msg = MIME::Lite::TT::HTML->new( 
            From        =>  'admin@example.com',
            To          =>  'test@yahoo.com', 
            Subject     =>  'Hello world', 
            Template    =>  {
                                text    =>  'test.txt',
                                html    =>  'test.html',
                            },
            TmplOptions =>  \%options, 
            TmplParams  =>  \%params, 
); 

my $smtp; 
$smtp = Net::SMTP::SSL->new($host, Port=>465) or die "Can't connect";
$smtp->auth($user, $pass) or die "Can't authenticate:".$smtp->message(
+);
$smtp->mail('admin@example.com') or die "Error:".$smtp->message();
$smtp->to('test@yahoo.com') or die "Error:".$smtp->message();
$smtp->data() or die "Error:".$smtp->message();
$smtp->datasend($msg->as_string) or die "Error:".$smtp->message();
$smtp->dataend() or die "Error:".$smtp->message();
$smtp->quit() or die "Error:".$smtp->message();
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All dogma is stupid.