Hi, mbethke,

I had changed the port No. however, I still get the error.

 $msg->send('smtp','smtp.live.com', Port => 587, AuthUser=>'username@hotmail.com', AuthPass=>'passwords');

Meanwhile, I had tested the Net::SMTP::TLS, and in that case, I can sent the text messages by hotmail, but I can not send the attachements(I can get the attachements, but badly encoded or bad file size etc), can you check my codes? Many thanks..

  use strict;
  use MIME::Lite;
  use Getopt::Std;
  use MIME::Base64;
  use Authen::SASL;
  use Net::SMTP::SSL;  
  use Net::SMTP::TLS;

  my $un='username@hotmail.com';
  my $pw='passwords';
  my $mh='smtp.live.com';
  my $pt=25; 
  my $from = 'username@hotmail.com'; 
  my $to = 'touser@gmail.com';


  my $mailer = new Net::SMTP::TLS(
    $mh,
    Port => $pt,
    User => $un,
    Password => $pw,
    Timeout => 60,
  ) or die "Cannot create a TLS mailer instance!\n";


  $mailer->mail($from);
  $mailer->to($to);
  $mailer->data();

  my $msg = MIME::Lite->new(
    From       => $from,
    'Reply-to' => $from,
    To         => $to,
    Subject    => "test",
    Type       => 'multipart/related'
  ) or die "Cannot create a new email instance!\n";

  $msg->attach(
    Type => 'TEXT',
    Data => "test messages",
  ) or die "Error adding TXT: $!\n";

 $msg->attach(
   Type        => 'aplication/pdf',
    Path        => 'test.pdf',
    Disposition => 'attachment'
  ) or die "Error adding PDF: $!\n";

  $mailer->datasend($msg->as_string);
  $mailer->dataend();
  $mailer->quit();
[download]

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