Sending E-mail that reaches the destination using PHP

Sending E-mail that reaches
the destination

Manuel Lemos
mlemos@acm.org

http://www.ManuelLemos.net/

http://www.phpclasses.org/mimemessage

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

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

PEAR Mail
●

SWIFT mailer
●

MIME message
●

Etc.
●

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

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

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();

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()

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()

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();

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;

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;

Mail() function alternatives
When the mail() function does not work well

smtp_mail()
●

sendmail_mail()
●

qmail_mail()
●

urgent_mail()
●

The path of the messages

Local SMTP Local queue Destination queue

SMTP Pickup

PHP script MTA Destination SMTP
mail()
Direct

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

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);

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);

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

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”>

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
●

Questions?

Manuel Lemos
mlemos@acm.org


References
MIME Message class
●

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/

Sending E-mail that reaches the destination using PHP

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Sending E-mail that reaches the destination using PHP