[php] Mail not sending with PHPMailer over SSL using SMTP

I am trying to use PHPMailer to send e-mails over SMTP but so far have had no luck. I've gone through a number of SO questions, PHPMailer tutorials and forum posts but still cannot get it to work. I'll document as many of my failed attempts as I can remember to save time, but firstly here is the code I am using:

<?php
    session_start();
    error_reporting(E_ALL);
    ini_set('display_errors','On');

    require('includes/class.phpmailer.php');
    include('includes/class.smtp.php');
    $mail = new PHPMailer(); 

    $name = $_POST["name"];
    $guests = $_POST["guests"];
    $time = $_POST["time"];

    $message = "<h1>".$name." has booked a table for ".$guests." at ".$time."</h1>";

    $mail->IsSMTP(); // telling the class to use SMTP
    $mail->Host       = "ssl://smtp.gmail.com"; // SMTP server
    $mail->SMTPDebug  = 1;                     // enables SMTP debug information (for testing)
    $mail->SMTPAuth   = true;                  // enable SMTP authentication
    $mail->Port       = 26;                    // set the SMTP port for the GMAIL server
    $mail->Username   = "[email protected]"; // SMTP account username
    $mail->Password   = "myPassword";        // SMTP account password
    $mail->SetFrom('[email protected]', 'James Cushing');
    $mail->AddReplyTo("[email protected]","James Cushing");
    $mail->Subject    = "PHPMailer Test Subject via smtp, basic with authentication";
    $mail->AltBody    = "To view the message, please use an HTML compatible email viewer!";
    $mail->MsgHTML($message)
    $address = "[email protected]";
    $mail->AddAddress($address, "James Cushing");

    if(!$mail->Send()) {
        echo "Mailer Error: " . $mail->ErrorInfo;
    } else {
        echo "Message sent!";
    }
?>

Firstly, when I run this code now I get two different errors. On my local server I get the error:
SMTP -> ERROR: Failed to connect to server: Operation timed out (60)
The following From address failed: [email protected] : Called Mail() without being connected
Mailer Error: The following From address failed: [email protected] : Called Mail() without being connected

I get moreorless the same error running the same code on my web server, but the first line is:
SMTP -> ERROR: Failed to connect to server: Network is unreachable (101)

Obviously it's worth pointing out that I'm not using the literal "[email protected]" but I've substituted my own email out for this post.

Things I've tried
- Using the iCloud SMTP server
- Using a different port
- Enabling the OpenSSL extension in my php.ini file
- Copying code from various PHPMailer examples
- Using Google's "DisplayUnlockCaptcha" system to enable connections
- Sending to and from different addresses - Removing the "@gmail.com" from the Username property - A number of other things I can't remember

This has now been driving me mad for about a day, so if anyone can solve it they will be a hero.

Thanks

I got a similar failure with SMTP whenever my client machine changes network connection (e.g., home vs. office network) and somehow restarting network service (or rebooting the machine) resolves the issue for me. Not sure if this would apply to your case, but just in case.

sudo /etc/init.d/networking restart   # for ubuntu

Firstly, use these settings for Google:

$mail->IsSMTP();
$mail->Host = "smtp.gmail.com";
$mail->SMTPAuth = true;
$mail->SMTPSecure = "tls"; //edited from tsl
$mail->Username = "myEmail";
$mail->Password = "myPassword";
$mail->Port = "587";

But also, what firewall have you got set up?

If you're filtering out TCP ports 465/995, and maybe 587, you'll need to configure some exceptions or take them off your rules list.

https://github.com/PHPMailer/PHPMailer/wiki/Troubleshooting

First, Google created the "use less secure accounts method" function:

https://myaccount.google.com/security

Then created the another permission:

https://accounts.google.com/b/0/DisplayUnlockCaptcha

Hope it helps.

Don't use SSL on port 465, it's been deprecated since 1998 and is only used by Microsoft products that didn't get the memo; use TLS on port 587 instead: So, the code below should work very well for you.

mail->IsSMTP(); // telling the class to use SMTP
$mail->Host       = "smtp.gmail.com"; // SMTP server

$mail->SMTPAuth   = true;                  // enable SMTP authentication
$mail->SMTPSecure = "tls";                 // sets the prefix to the servier
$mail->Host       = "smtp.gmail.com";      // sets GMAIL as the SMTP server
$mail->Port       = 587;                   // set the SMTP port for the