#!/usr/bin/perl
use strict;
use warnings;
use Net::SMTPS;
use MIME::Base64 qw( encode_base64 );

my $from = 'Tester <tester@hotmail.com>';
my $to   = shift || 'tester@hotmail.com';
my $pic  = shift || 'test.jpg';

# Email connection.
my $username = 'tester@hotmail.com';
my $password = 'foo';
my $smtp = Net::SMTPS->new('outlook.com', Port => 587,  doSSL => 'starttls', SSL_version=>'TLSv1');
$smtp->auth ( $username, $password ) or die "Could not authenticate with Outlook.\n";
print "Sending mail\n";

# Email header.
my $boundary = 'frontier';
$smtp->mail($from);
$smtp->recipient($to, { SkipBad => 1 });
$smtp->data();
$smtp->datasend("To: $to\n");
$smtp->datasend("From: $from\n");
$smtp->datasend("Subject: Perl Test Email\n");
$smtp->datasend("MIME-Version: 1.0\n");
$smtp->datasend("Content-type: multipart/mixed;\n\tboundary=\"$boundary\"\n");
$smtp->datasend("\n");

# Email body.
$smtp->datasend("--$boundary\n");
$smtp->datasend("Content-type: text/plain\n");
$smtp->datasend("Content-Disposition: quoted-printable\n");
$smtp->datasend("Testing Perl email.\n");

# Email attachment.
$smtp->datasend("--$boundary\n");
$smtp->datasend("Content-Type: image/jpeg; name=\"$pic\"\n");
$smtp->datasend("Content-Transfer-Encoding: base64\n");
$smtp->datasend("Content-Disposition: attachment; filename=\"$pic\"\n");
$smtp->datasend("\n");
open(my $fh2, '<', $pic) || die("Could not open Jpg file!");
   binmode($fh2);
   local $/=undef;
   while (read($fh2, my $chunk, 72*57)) {
      my $buf = &encode_base64( $chunk );
      $smtp->datasend($buf);
   }
close($fh2);

$smtp->datasend("\n");
$smtp->datasend("--$boundary--\n");
$smtp->dataend();
$smtp->quit;

print "Mail sent\n";
exit;