phpMailer send a smtp email - php

Question

I am trying to send an email using phpMailer.
I have downloaded and put the files in "path2".
The php program has 3 inputs: $email, $subject and $body.
Here is the error code when ran:
2014-06-24 15:48:18 SMTP ERROR: Failed to connect to server: A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond. (10060) SMTP connect() failed. Mailer Error: SMTP connect() failed.
Here is my code:
<?php
require_once("..\path2\class.phpmailer.php");
date_default_timezone_set('America/Eastern');
include("..\path2\class.smtp.php");
$mail = new PHPMailer();
$mail->IsSMTP();
$mail->SMTPDebug = 1;
$mail->SMTPAuth = True;
$mail->SMTPSecure = "SSL";
$mail->Host = "smtp.live.com";
$mail->Port = 465;
$mail->Username = "self#live.com";
$mail->Password = "pass1";
$mail->From="self#live.com";
$mail->Subject = $subject;
$mail->Body=$body;
$mail->AddAddress($email);
if(!$mail->Send()) {
echo "Mailer Error: " . $mail->ErrorInfo;
} else {
echo "Message sent!";
}
?>

Answer 1

Telnet isn't very useful for testing encrypted connections - openssl is better. Try this on your server:
openssl s_client -crlf -connect smtp.live.com:465
That's currently not connecting for me from multiple countries, so perhaps Microsoft finally heeded the deprecation of SSL on port 465 back in 1998... Try this instead:
openssl s_client -starttls smtp -crlf -connect smtp.live.com:587
That's working well for me, so I suggest you make these changes to your code:
$mail->SMTPSecure = "tls";
$mail->Port = 587;