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    <p>I might be wrong because I don't use IIS but the code you provided would actually use a native MTA not SMTP. As far as I know you have to use the <code>IsSMTP()</code> method to let PHPMailer know that you intend to use SMTP.</p> <p>Something like this:</p> <pre><code>&lt;? $path_of_attached_file = "Images/marsbow_pacholka_big.jpg"; require 'include/PHPMailer_5.2.1/class.phpmailer.php'; try { $mail = new PHPMailer(true); //New instance, with exceptions enabled $body = $message; //"&lt;p&gt;&lt;b&gt;Test&lt;/b&gt; another test 3.&lt;/p&gt;"; $mail-&gt;IsSMTP(); // telling the class to use SMTP $mail-&gt;Host = "mail.yourdomain.com"; // SMTP server $mail-&gt;SMTPDebug = 2; $mail-&gt;SMTPAuth = true; // enable SMTP authentication $mail-&gt;Host = "mail.yourdomain.com"; // sets the SMTP server $mail-&gt;Port = 25; // set the SMTP port $mail-&gt;Username = "yourname@yourdomain"; // SMTP account username $mail-&gt;Password = "yourpassword"; // SMTP account password $mail-&gt;AddReplyTo("admin@example.com","Admin"); $mail-&gt;From = "admin@example.com"; $mail-&gt;FromName = "Admin"; $mail-&gt;AddAddress($to); $mail-&gt;Subject = "First PHPMailer Message"; $mail-&gt;AltBody = "To view the message, please use an HTML compatible email viewer!"; // optional, comment out and test $mail-&gt;WordWrap = 80; // set word wrap $mail-&gt;MsgHTML($body); $mail-&gt;IsHTML(true); // send as HTML if($attach){ $mail-&gt;AddAttachment($path_of_attached_file); } $mail-&gt;Send(); echo 'Message has been sent.'; } catch (phpmailerException $e) { echo $e-&gt;errorMessage(); } ?&gt; </code></pre>
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    1. COYeah, that fixed it. Which is slightly weird because mail() is configured to go out through SMTP in php.ini... I wish I knew why this didn't work this way. Before I was using PHPMail I was trying to encode my own headers and it was putting the contents of the file into the body of the email, instead of as an attachment. So message size isn't the problem I don't think.
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    2. COIt also makes me a little nervous that the email said sent, but never showed up. I just sent myself a 13mb attachment so hopefully that means it is fixed, but I wish I knew what happened to all those tests before. there were no error log entries in php or smtp that I could find.
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    3. COThere are many quirks when it comes to PHP+IIS combination and this might just be one of them. Though as I already said I am not that much familiar with IIS.
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