Swiftmailer Erroring Out

Question

I'm having some trouble with swiftmailer. It keeps crashing on me, but if I take out the ->sentTo it doesn't error out but I also can't receive an Email.

I'm confused as to what I am doing wrong.

require_once 'lib/swift_required.php';

// Using smtp
//$transport = Swift_SmtpTransport::newInstance('my_smtp_host.com', 25)

//Using Gmail
$transport = Swift_SmtpTransport::newInstance('smtp.gmail.com', 465, "ssl") 
  ->setUsername('***') // or your gmail username
  ->setPassword('***'); // or your gmail password

// Create the Mailer using your created Transport
$mailer = Swift_Mailer::newInstance($transport);

// Create a message
$message = Swift_Message::newInstance($subject)
  ->setFrom(array($email => $name))
  ->setTo(array('John.Doe@gmail.com' => 'John Doe'))
   ->setBody($content, 'text/html');

$message->attach(
Swift_Attachment::fromPath($_FILES['userfile']['name'])->setFilename($pic['tmp_name'])
);

// Send the message
$result = $mailer->send($message);

?>

Fatal error:

Uncaught exception 'Swift_TransportException' with message 'Failed to authenticate on SMTP server with username "...." using 2 possible authenticators' in ../lib/classes/Swift/Transport/Esmtp/AuthHandler.php:184 

Stack trace: 

0 ../lib/classes/Swift/Transport/Esmtp/EsmtpTransport.php(312): Swift_Transport_Esmtp_AuthHandler->afterEhlo(Object(Swift_SmtpTransport)) 

1 ../lib/classes/Swift/Transport/AbstractSmtpTransport.php(120): Swift_Transport_EsmtpTransport->_doHeloCommand() 

2 ../lib/classes/Swift/Mailer.php(80): Swift_Transport_AbstractSmtpTransport->start() 

3 upload.php(73): Swift_Mailer->send(Object(Swift_Message)) 

4 {main} thrown in lib/classes/Swift/Transport/Esmtp/AuthHandler.php on line 184

Answer 1

Had to change the message attachment to this:

$message->attach(
    Swift_Attachment::fromPath($theDirectory)->setFilename($fileNameForEmail)
    );

    // Send the message
    $result = $mailer->send($message);
}
else{
        echo 'The file you have chosen is invalid. Please go back and try again.';
}

Answer 2

This:

Failed to authenticate on SMTP server with username "...." using 2 possible authenticators

... means exactly what it says. Gmail did not accept your username and password, either because they are wrong or because you failed to provide some required parameter.

Host name, port and encryption are correct according to other questions at Stack Overflow and my own tests. So probably issues include:

1. You provided an incorrect user name.
2. You provided an incorrect password.
3. If you've enabled two-way authentication, you need to generate an application specific password. This video explains how.

Once you fix this, you'll probably get the following exception:

Uncaught exception 'Swift_IoException' with message 'Unable to open file for reading []'

... triggered by this code:

Swift_Attachment::fromPath($_FILES['userfile']['name'])

The reason if that you are reading the wrong item from the $_FILES array: fromPath() expects a file system path to read but $_FILES['userfile']['name'] contains the original name of the file on the client machine.