PHPMailer problem connecting to smtp.mail.emea.microsoftonline.com

Question

I'm getting the following error when trying to send an email from a web server running W2K server 2003 to smtp.mail.emea.microsoftonline.com

SMTP -> FROM SERVER:220 smtp.mail.emea.microsoftonline.com Microsoft ESMTP MAIL Service ready at Thu, 8 Oct 2009 01:00:53 -0700 
SMTP -> FROM SERVER: 250-smtp.mail.emea.microsoftonline.com Hello [78.109.167.122] 250-SIZE 31457280 250-PIPELINING 250-DSN 250-ENHANCEDSTATUSCODES 250-STARTTLS 250-AUTH 250-8BITMIME 250-BINARYMIME 250 CHUNKING 
SMTP -> ERROR: AUTH not accepted from server: 504 5.7.4 Unrecognized authentication type 
SMTP -> FROM SERVER:250 2.0.0 Resetting 
SMTP Error: Could not authenticate.

Can anyone spot what is wrong? I have the the following set in php.ini as well:

[mail function]
; For Win32 only.
SMTP = smtp.mail.emea.microsoftonline.com
smtp_port = 587
; For Win32 only.
sendmail_from = [email protected]

---

require_once('class.phpmailer.php');

$mail = new PHPMailer(true); // the true param means it will throw exceptions on errors, which we need to catch

$mail->IsSMTP(); // telling the class to use SMTP

try {
  $mail->Host       = "smtp.mail.emea.microsoftonline.com"; // SMTP server
  $mail->SMTPDebug  = 2;                     // enables SMTP debug information (for testing)
  $mail->SMTPAuth   = true;                  // enable SMTP authentication
  //$mail->SMTPSecure = "ssl";                 // sets the prefix to the servier
  $mail->Port       = 587;                   // set the SMTP port for the server
  $mail->Username   = "[email protected]";  // username
  $mail->Password   = "Password";            // password
  $mail->AddReplyTo('[email protected]', 'First Last');
  $mail->AddAddress('[email protected]', 'John Doe');
  $mail->SetFrom('[email protected]', 'First Last');
  $mail->AddReplyTo('[email protected]', 'First Last');
  $mail->Subject = 'PHPMailer Test Subject via mail(), advanced';
  $mail->AltBody = 'To view the message, please use an HTML compatible email viewer!'; // optional - MsgHTML will create an alternate automatically
  $mail->MsgHTML(file_get_contents('examples/contents.html'));
  $mail->Send();
  echo "Message Sent OK</p>\n";
} catch (phpmailerException $e) {
  echo $e->errorMessage(); //Pretty error messages from PHPMailer
} catch (Exception $e) {
  echo $e->getMessage(); //Boring error messages from anything else!
}

Answer 1

Try these manual steps first to see if you can connect at all:

http://technet.microsoft.com/en-us/library/aa995718%28EXCHG.65%29.aspx

Also, this page: http://www.gilham.org/Blog/Lists/Posts/Post.aspx?List=aab85845%2D88d2%2D4091%2D8088%2Da6bbce0a4304&ID=665

says that: The FROM address must use a SMTP domain of type “Authoritative” – this can be confirmed in Microsoft Online Administration Center, under the Users - Domains tab.

Answer 2

I've same problem some month ago. And the error caused by our SMTPSecure is used ntlm. Don't forget to relay your mail server which it's allow to sent and receive mail from the web. And recheck your account email and the password that is it right?