PHPMailer loads a while, then gives 500 - Internal server error

Question

I am trying to setup a php page to automatically send a verification email. I would like to use the gmail smtp servers, and everywhere I've looked suggests to use PHPMailer. I installed it and used the following example code:

ini_set('display_errors', 1);
error_reporting(E_ALL);
require_once ("incl\PHPMailer\PHPMailerAutoload.php");

$mail = new PHPMailer();
$mail->IsSMTP();
$mail->SMTPAuth = true;
$mail->SMTPSecure = "tls";
$mail->Host = "smtp.gmail.com";
$mail->Port = 587;
$mail->Username = "[email protected]";
$mail->Password = "mypassword";
$mail->SetFrom('[email protected]','Me');
$mail->AddAddress("[email protected]");
$mail->Subject = "Verify your email";
$mail->Body = "Thank you for signing up.  Please verify your email using the link below:";
$mail->IsHTML (true);

if($mail->Send()){
    echo "Success";
}else{
    echo "Error";
}

When trying to access the page via Firefox, the page will load for a few minutes, then give this error:

500 - Internal server error.
There is a problem with the resource you are looking for, and it cannot be displayed.

The server is Windows Server 2008 R2 Standard running IIS 7.5 and PHP Version 5.5.8. I can access all other pages without issues, but trying to call $mail->Send() seems to be timing out or something. I know this because I commented every line and slowly added pieces back in and $mail->Send() is the line that causes the behavior.

My Google abilities are failing me here as I simply cannot figure out how to make this work. Any ideas on what might be wrong?

Update

I opened the server log then tried loading the page again, but no new errors were added to the log. However, I noticed the following errors from today in System32\LogFiles\httperr1.log

2014-10-27 06:29:21 1.161.23.122 3148 212.83.145.123 80 HTTP/1.0 CONNECT mx2.mail2000.com.tw:25 400 - URL -  
2014-10-27 10:10:12 95.183.244.244 33553 212.83.145.123 80 HTTP/1.1 GET / 400 - Hostname -
2014-10-27 11:25:25 207.38.185.197 51157 212.83.145.123 80 HTTP/1.1 GET /tmUnblock.cgi 400 - Hostname -
2014-10-27 12:46:21 1.168.221.158 7952 212.83.145.123 80 - - - - - Timer_ConnectionIdle -

UPDATE 2

I am positive that my gmail account details are correct and have tested sending from it using Thunderbird on the server. When trying to sent without secured methods, as suggested in this comment I get this error:

MAIL FROM command failed,550,5.7.3 Requested action aborted; user not authenticated

My PHP Mailer version is 5.2.9 and I've now also tried the following:

• Using \\ in file paths instead of \
  • No change
• Including class.phpmailer.php instead of PHPMailerAutoload.php
  • Fatal error: Class 'SMTP' not found in C:\inetpub\wwwroot\incl\PHPMailer\class.phpmailer.php on line 1195
• Using ssl over port 465
  • SMTP connect() failed
• Sending with a hotmail address over port 25 with $mail->SMTPAuth = false;
  • MAIL FROM command failed,550,5.7.3 Requested action aborted; user not authenticated

Update 3

After reloading the problem page, I checked through the Event Viewer and saw a new entry in Windows Logs -> System:

PHP Error : syntax error, unexpected BOOL_TRUE in C:\PHP\php.ini on line 101

That line is:

php_flag display_errors on

Answer 1

Looks like you're dealing with bunch of issues and here is a checklist: you're having issues with ssl, the actual mail software and credentials. It became an issue of 3 from one main issue and I'm guessing you don't either have your credentials typed in correctly or your open ssl isn't setup and you're also having issues using the mail software.

535 535 5.7.3 Authentication Unsuccessful means auth is unsuccessful, check your credentials username and password.

550 error code, it means that the receiving system could not deliver your email to the user to whom it was addressed because the mailbox is unavailable.

There are plenty of other solutions to resolve your issue. Why don't you try something more simple instead of using the autoload PHPMailerAutoload.php. Create a new file and place the code below, create a message body (test_message.html) and call it from the browser to test gmail smtp with the gmail credentials. This is a snippet from PHPMailer on how to use it with gmail smtp and it shouldn't go wrong if you have everything filled in correctly.

<?php
    require_once('../class.phpmailer.php');
    //include("class.smtp.php"); // optional, gets called from within class.phpmailer.php if not already loaded

    $mail             = new PHPMailer();

    $body             = file_get_contents('test_message.html');
    $body             = eregi_replace("[\]",'',$body);

    $mail->IsSMTP(); // telling the class to use SMTP
    $mail->Host       = "mail.yourdomain.com"; // SMTP server
    $mail->SMTPDebug  = 2;                     // enables SMTP debug information (for testing)
                                               // 1 = errors and messages
                                               // 2 = messages only
    $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 GMAIL server
    $mail->Username   = "[email protected]";  // GMAIL username
    $mail->Password   = "yourpassword";            // GMAIL password

    $mail->SetFrom('[email protected]', 'First Last');

    $mail->AddReplyTo("[email protected]","First Last");

    $mail->Subject    = "PHPMailer Test Subject via smtp (Gmail), basic";

    $mail->AltBody    = "To view the message, please use an HTML compatible email viewer!"; // optional, comment out and test

    $mail->MsgHTML($body);

    $address = "[email protected]";
    $mail->AddAddress($address, "John Doe");

    $mail->AddAttachment("images/phpmailer.gif");      // attachment
    $mail->AddAttachment("images/phpmailer_mini.gif"); // attachment

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

If you're getting user auth error, then your credentials aren't typed in correctly. If that's not the issue, you'll get an ssl error if you're not using the right port.

If there are software issues with include, you should try something better.

I was debating this morning if I should should PHPMailer, ended up using Swiftmailer which worked right after I installed it with PHPComposer.

My Internal mail server is extremely picky and has ton of firewall settings and rules on hardware and software level and I was surprised it didn't give me any problems; the emails were being sent right away without any problems on port 587.

require_once 'vendor/swiftmailer/swiftmailer/lib/swift_required.php';
$transport = Swift_SmtpTransport::newInstance('mail.hellog***.com', 587)
  ->setUsername('apache@hellog***.com')
  ->setPassword('apa******')
  ;

This is what you need for gmail:

$transporter = Swift_SmtpTransport::newInstance('smtp.gmail.com', 465, 'ssl')
  ->setUsername($this->username)
  ->setPassword($this->password);

$this->mailer = Swift_Mailer::newInstance($transporter);

If none of what you like, you can try phpgmailer: https://github.com/GregDracoulis/LectureBank/tree/master/phpgmailer

here is an example on how to use it: http://www.vulgarisoverip.com/2006/10/13/update-send-email-with-php-and-gmail-hosted-for-your-domain/

this class is dedicated for gmail use.

If all your problems and issues relate to openSSL, you should follow the steps below:

1. Make sure the OpenSSL module DLL file is included in the PHP installation:

C:\user>dir \local\php\ext\php_openssl.dll

Directory of C:\local\php\ext

php_openssl.dll

2. Create the PHP configuration file, \local\php\php.ini, if it does not exist:

C:\user>copy \local\php\php.ini-production \local\php\php.ini

    1 file(s) copied.

3. Enable the OpenSSL module by editing the configuration file with a text editor. You need to remove the comment maker (;) on two configuration lines:

...

; Directory in which the loadable extensions (modules) reside.
; http://php.net/extension-dir
; extension_dir = "./"
; On windows:
extension_dir = "ext"

...
extension=php_openssl.dll

...

That’s it. You should be all set setting up openSSL on your Windows IIS WebServer. Follow these options and steps, it could be your issue.