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Sending E-mail that reaches
      the destination

             Manuel Lemos
             mlemos@acm.org

       http://ww...
The problems
    Sending e-mail is fundamental
●



    PHP native support for sending e-mail is
●

    deficient
    The ...
Solution
    Ready to use PHP components for sending
                      e‑mail
    PHPMailer
●



    PEAR Mail
●



  ...
What is MIME?
    Multipurpose Internet Mail Extensions
●




    Standards for sending E-mail messages
●




    Defined ...
MIME message class

      PHP class to compose and send e-mail
    Sends messages with text and HTML using
●

    any char...
Text message
require('email_message.php');
$m = new email_message_class;
$m->SetEncodedHeader('Subject', 'This is the subj...
HTML message
$html =
  “<html><head><title>Messagm</title></head><body>Hello
  Joe,<br />n<br />nThis is the message.</bod...
HTML messages with
            embedded images
$image=array(                        $m->CreateQuotedPrintableHTMLPart
    ...
Message with attached files
$attachment=array(
 'Data'=>'This is an attachment called attachment.txt',
 'Name'=>'attachmen...
Sending via SMTP
 Supports several types of authentication using
   the SASL classes: LOGIN, MD5, NTLM, etc.
require('sasl...
Sending via sendmail, qmail
   and Microsoft Exchange
          Faster delivery to the MTA queue
require('sendmail_message...
Mail() function alternatives
    When the mail() function does not work well

    smtp_mail()
●




    sendmail_mail()
●
...
The path of the messages

       Local SMTP            Local queue   Destination queue

SMTP                Pickup

      ...
The best delivery methods

1.Drop a message file in the local queue

2.Pass to MTA with the mail function (sendmail)

3.Pa...
Optimizing the delivery of
    non‑personalized newsletters
$list = array(
 'peter@here.com'=>'Peter',
 'paul@there.com'=>...
Optimizing the delivery of
     personalized newsletters
$m->SetBulkMail(1);
$m->cache_body = 0;
$template = 'Hello {name}...
Handling returned messages
1.Set the Return-Path message header to an
  address associated with a POP3 mailbox
2.Periodica...
Know when a message was
          received
         Techniques that do not always work

1.Set the Disposition-Notification...
Avoid confusion with SPAM
 What types of messages you should not send?
● Sent from an IP address without reverse DNS

  re...
Questions?


        Manuel Lemos
       mlemos@acm.org

http://www.phpclasses.org/mimemessage
References
    MIME Message class
●


    http://www.phpclasses.org/mimemessage
    SMTP client class
●


    http://www.p...
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Sending E-mail that reaches the destination using PHP

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Slides of a presentation about the PHP MIME message composing and sending class. It teaches how to compose and send e-mail according to the Internet e-mail standards and without problems of messages not reaching the destination recipients, efficient bulk mailing of personalized and non-personalized messages, handling bounced messages, knowing when messages are viewed, and avoiding messages being confused with SPAM.

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Sending E-mail that reaches the destination using PHP

  1. 1. Sending E-mail that reaches the destination Manuel Lemos mlemos@acm.org http://www.ManuelLemos.net/ http://www.phpclasses.org/mimemessage
  2. 2. The problems Sending e-mail is fundamental ● PHP native support for sending e-mail is ● deficient The Internet e-mail standards are complicated ● Incorrectly composed messages are ● discarded Correctly composed messages are confused ● with SPAM
  3. 3. Solution Ready to use PHP components for sending e‑mail PHPMailer ● PEAR Mail ● SWIFT mailer ● MIME message ● Etc. ●
  4. 4. What is MIME? Multipurpose Internet Mail Extensions ● Standards for sending E-mail messages ● Defined by many RFC documents: Request ● For Comments New RFC document versions are compatible ● with past versions
  5. 5. MIME message class PHP class to compose and send e-mail Sends messages with text and HTML using ● any character set Embeds related files: images, CSS, etc.. ● May attach multiple files ● Optimized for sending newsletters to many ● recipients
  6. 6. Text message require('email_message.php'); $m = new email_message_class; $m->SetEncodedHeader('Subject', 'This is the subject'); $m->SetEmailEncodedHeader('From', 'john@here.com', 'John'); $m->SetEmailEncodedHeader('To', 'joe@there.com', 'Joe'); $text = “Hello Joe,nnThis is the message.”; $m->AddQuotedPrintableTextPart($text); $m->Send();
  7. 7. HTML message $html = “<html><head><title>Messagm</title></head><body>Hello Joe,<br />n<br />nThis is the message.</body></html>”; $text = strip_tags($html); $m->CreateQuotedPrintableHTMLPart($html, '', $h); $m->CreateQuotedPrintableTextPart($text, '', $t); $alternatives = array($t, $h); $m->AddAlternativeMultipart($alternatives); $m->Send()
  8. 8. HTML messages with embedded images $image=array( $m->CreateQuotedPrintableHTMLPart ($html, '', $h); 'FileName'=>'image.gif', 'Content-Type' => $text = strip_tags($html); 'automatic/name', $m->CreateQuotedPrintableTextPart 'Disposition'=>'inline' ($text, '', $t); ); $alternatives = array($t, $h); $e->CreateFilePart($image, $i); $m->AddAlternativeMultipart ($alternatives); $url = 'cid:'. $related = array( $alternatives, $m->GetPartContentID($i); $i, $html = quot;<html> ); <head><title>Message</title> $m->AddRelatedMultipart </head><body><img src=”$url” /> ($related); Hello Joe,<br />n<br />nThis is the message.</body></html>quot;; $m->Send()
  9. 9. Message with attached files $attachment=array( 'Data'=>'This is an attachment called attachment.txt', 'Name'=>'attachment.txt', 'Content-Type'=>'automatic/name', 'Disposition'=>'attachment', ); $m->AddFilePart($attachment); $attachment=array( 'FileName'=>'attachment.zip', 'Content-Type'=>'automatic/name', 'Disposition'=>'attachment', ); $m->AddFilePart($attachment); $m->Send();
  10. 10. Sending via SMTP Supports several types of authentication using the SASL classes: LOGIN, MD5, NTLM, etc. require('sasl.php'); require('smtp.php'); require('smtp_message.php'); $m = new smtp_message_class; $m->smtp_host = 'smtp.gmail.com'; $m->smtp_port = 465; $m->smtp_ssl = 1; $m->smtp_user = 'some_user'; $m->smtp_password = 'some_password'; $m->direct_delivery = 0;
  11. 11. Sending via sendmail, qmail and Microsoft Exchange Faster delivery to the MTA queue require('sendmail_message.php'); $m = new sendmail_message_class; $m->delivery_mode = SENDMAIL_DELIVERY_DEFERRED; require('qmail_message.php'); $m = new qmail_message_class; require('pickup_message.php'); $m = new pickup_message_class;
  12. 12. Mail() function alternatives When the mail() function does not work well smtp_mail() ● sendmail_mail() ● qmail_mail() ● urgent_mail() ●
  13. 13. The path of the messages Local SMTP Local queue Destination queue SMTP Pickup PHP script MTA Destination SMTP mail() Direct
  14. 14. The best delivery methods 1.Drop a message file in the local queue 2.Pass to MTA with the mail function (sendmail) 3.Pass to the local SMTP server 4.Direct delivery to the destination SMTP server
  15. 15. Optimizing the delivery of non‑personalized newsletters $list = array( 'peter@here.com'=>'Peter', 'paul@there.com'=>'Paulo', 'mary@overthere.com'=>'Mary' ); $m->SetBulkMail(1); $m->cache_body = 1; foreach($list as $email => $name) { $m->SetEncodedEmailHeader('To', $email, $name); $m->Send(); } $m->SetBulkMail(0);
  16. 16. Optimizing the delivery of personalized newsletters $m->SetBulkMail(1); $m->cache_body = 0; $template = 'Hello {name}, ...'; $m->CreateQuotedPrintableTextPart($template, '', $part_template); $m->AddPart($part_template); foreach($list as $email => $name) { $m->SetEncodedEmailHeader('To', $email, $name); $text = str_replace('{name}', $name, $template); $m->CreateQuotedPrintableTextPart($text, '', $personalized); $m->ReplacePart($part_template, $personalized); $m->Send(); } $m->SetBulkMail(0);
  17. 17. Handling returned messages 1.Set the Return-Path message header to an address associated with a POP3 mailbox 2.Periodically poll that mailbox using a POP3 client class 3.Process the returned messages with the MIME parser class 4.Unsubscribe from the newsletters the e‑mail addresses that are returning the messages
  18. 18. Know when a message was received Techniques that do not always work 1.Set the Disposition-Notification-To message header to an address to which reception notices will be sent 2.Insert a beacon image in an HTML message using the URL of a script that accounts messages that are viewed by recipients <img src=”http://www.meusite.com.br/conta.php?usuario=joao@ali.com.br”>
  19. 19. Avoid confusion with SPAM What types of messages you should not send? ● Sent from an IP address without reverse DNS record (PTR) or that is listed in blacklists ● The recipient e-mail addresses are in Bcc Only with an HTML part or has invalid HTML ● With beacon image URL that has parameters ● Link URLs do not match anchor text URL ● Do not pass SpamAssassin checks ●
  20. 20. Questions? Manuel Lemos mlemos@acm.org http://www.phpclasses.org/mimemessage
  21. 21. References MIME Message class ● http://www.phpclasses.org/mimemessage SMTP client class ● http://www.phpclasses.org/smtpclass SASL authentication class ● http://www.phpclasses.org/sasl POP3 client class ● http://www.phpclasses.org/pop3class MIME parser class ● http://www.phpclasses.org/mimeparser Verify IP addresses in multiple blacklists ● http://openrbl.org/ SpamAssassin ● http://spamassassin.apache.org/

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