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 = "myemail@gmail.com";
$mail->Password = "mypassword";
$mail->SetFrom('myemail@gmail.com','Me');
$mail->AddAddress("ToAddress@gmail.com");
$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   = "yourusername@gmail.com";  // GMAIL username
    $mail->Password   = "yourpassword";            // GMAIL password

    $mail->SetFrom('name@yourdomain.com', 'First Last');

    $mail->AddReplyTo("name@yourdomain.com","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 = "whoto@otherdomain.com";
    $mail->AddAddress($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.

Answer 2

This problem is slashes ( \ )

Edit

require_once ("incl\\PHPMailer\\PHPMailerAutoload.php");

Answer 3

I have tried with you code, and i have only changed this line :

require_once ("incl\PHPMailer\PHPMailerAutoload.php");

by this one :

require_once ("incl\PHPMailer\class.phpmailer.php");

And it was worked successfully.
Also you should keep attention about your PHPMailer version and your PHP version.
Have you tried to send an email with not secured method ?
Are you sure that your google credentials are valid ?

UPDATED
From the command line of your server, what is the output of this command and how much time that it takes to respond

telnet smtp.gmail.com 587

Answer 4

I wonder if you are running into the same issue that this question ran into. Google actively frowns on people using Gmail as their own personal SMTP server.

http://www.labnol.org/internet/email/gmail-daily-limit-sending-bulk-email/2191/

Google also limits the number of email messages that you can send through your Gmail account in a day. If you exceed the daily quota, Google may temporarily disable your Gmail account without any warnings and you may have to wait for up to 24 hours before you can regain access to your Gmail mailbox.

I could see an error like that potentially producing a 500 error.

Answer 5

From the comments to the question, it seems pretty clear that this issue is OpenSSL related.

You mentioned that you already have extension=php_openssl.dll uncommented, but phpinfo() does show it not beeing loaded.

Some thoughts:

• Have you restarted the webserver, after uncommenting the openssl php module in your php.ini?

  This is the really obvious one, but still worth mentioning. The php.ini is loaded on start-up, and not doing a service restart is simply a common mistake.

• Check the value of Loaded Configuration File in phpinfo()

  If this is not the same location than the php.ini which you have edited, it also becomes clear why it has not been loaded. Also following lines from phpinfo() might be worth checking.

  • Configuration File (php.ini) Path
  • Loaded Configuration File
  • Scan this dir for additional .ini files

There are other things too which can be done like uninstalling and reinstalling OpenSSL, but it might be good to check these more obvious things first.

Further thoughts:

• Checking the error logs

  For php the path can (again) be found in your phpinfo(). Look for the value of error_log and check the latest entries, right after you tried to reload your page.

  Also you may wanna check the log files of IIS. If you don't know the path look in the IIS Manager, select the computer on the left pane, and in the middle pane, go under "logging" in the IIS area. Usually these will point to something like C:\inetpub\logs\LogFiles or C:\Windows\System32\LogFiles with a subfolder like W3SVC[x] where [x] is the website ID. (Will be just 1 if you only have one page, otherwise check the top level websites folder in IIS Manager, view the lists of sites in the right hand pane, it's the App ID)

Answer 6

Setting Up and Configuring IIS

Start by going to the ServerManager on you Server. Most often this is the server you’ll be running your php website on. Go to Add features in the Features summary section. Check SMTP Services in the Add Features Wizard and hit install. Now wait for the installation to finish. Open IIS6 (or IIS7) Manager under Administrative Tools -> Internet Information Services 6.0 in the Start Menu, the configuration of SMTP makes use of the management console from IIS6. Under [SMTP Virtual Server], click your right mouse button and select properties from the context menu. Go to the Access Tab and hit the Relay button.Add a new entry to the list by clicking the Add button and enter 127.0.0.1 (or your web server's IP) in the single computer entry field. Hit Ok two times to apply the new settings.

Configuring Php

To make Php send emails you need to make some configurations. Basically there are two options. In case you’re only going to use the SMTP server in a single project and do not want it to interfere with other projects, you can set the configuration from within your php code by adding the following lines anywhere before sending the email:

ini_set('SMTP','localhost' ); 
ini_set('sendmail_from', 'administrator@YourWebsite.com');

Another way, to make global use of these settings, add the next lines to your php.ini file.

[mail function]
SMTP = localhost
sendmail_from = me@example.com

Make sure you restart your server after making these changes, to be sure they’re loaded.

This solution is provided here http://geekswithblogs.net/tkokke/archive/2009/05/31/sending-email-from-php-on-windows-using-iis.aspx on how to set up IIS and php and was provided as answer to this question 500 error when trying to use the MAIL function

Answer 7

Try to use SSL encryption with a port 465:

$mail->SMTPSecure = "ssl";
$mail->Host = "smtp.gmail.com";
$mail->Port = 465;

Answer 8

Warning: require_once(mailer/PHPMailerAutoload.php): failed to open stream: No such file or directory in....

This is the way I had my file routed

Before: require_once "mailer/PHPMailerAutoload.php";

After: require_once "../mailer/PHPMailerAutoload.php";

...Same process you would normally do to link an img as background using css.