PHP E-Mailer won’t work unless sender e-mail address is in safe senders list

18. October 2013 · Write a comment · Categories: Hotmail, Outlook.com · Tags:
Sending an e-mail using a PHP script where reply-to:, return-path: and from: addresses of *** Email address is removed for privacy *** or *** Email address is removed for privacy *** seem to not get through to my live webmail both inbox or junk (Now Outlook I think) unless the sender address is in the 'Safe Senders' list in webmail. if I use google webmail logged onto *** Email address is removed for privacy *** and send it to hotmail to *** Email address is removed for privacy *** it gets through without having *** Email address is removed for privacy *** in the safe senders list in live.

Why is there a difference? Why does the e-mail from Google webmail get through when the PHP script doesn't when *** Email address is removed for privacy *** is NOT defined in the safe senders list? Is there something missing in the PHP header statement?

When the return-path:, from: and reply-to: fields are set to *** Email address is removed for privacy *** the e-mail gets through to *** Email address is removed for privacy *** without *** Email address is removed for privacy *** being set in the safe senders list under *** Email address is removed for privacy *** webmail.

This problem makes no sense, yet I can consistently reproduce the problem every time. Why do some sender e-mail addresses work in the PHP script without defining in the safe senders list where other e-mail addresses don't!?

The PHP Code:

    $headers = "From:" . stripslashes(trim($email_from)) . "\r\n";
    $headers .= "Reply-To:" . stripslashes(trim($reply_to)) . "\r\n";
    $headers .= "Return-Path:" . stripslashes(trim($return_path)) . "\r\n";
    $headers .= "X-Mailer: PHP/" . phpversion() . "\n";
    $headers .= "MIME-Version: 1.0 \r\n";
    $headers .= "Content-Type: text/html; charset=ISO-8859-1 \r\n";

Is there something additional I need to put in the $headers code to get the e-mail accepted by the hotmail / outlook / live servers? Apparently the google webmail seems to have it right somehow

Dumped E-Mail Headers from Outlook
==========================

Using the PHP Script to send to *** Email address is removed for privacy *** (Only when *** Email address is removed for privacy *** in safe senders list)
-------------------------------------------------------------------------------------------------------------------------------

Delivered-To: *** Email address is removed for privacy ***
Received: by 10.112.201.42 with SMTP id jx10csp61747lbc;
        Fri, 18 Oct 2013 13:56:36 -0700 (PDT)
X-Received: by 10.68.175.33 with SMTP id bx1mr4888632pbc.21.1382129795477;
        Fri, 18 Oct 2013 13:56:35 -0700 (PDT)
Return-Path: <*** Email address is removed for privacy ***>
Received: from srv3.com.au (216.185.104.219-static.reverse.softlayer.com. [216.185.104.219])
        by mx.google.com with ESMTPS id hj4si2343722pac.242.2013.10.18.13.56.34
        for <*** Email address is removed for privacy ***>
        (version=TLSv1 cipher=RC4-SHA bits=128/128);
        Fri, 18 Oct 2013 13:56:35 -0700 (PDT)
Received-SPF: softfail (google.com: domain of transitioning *** Email address is removed for privacy *** does not designate 216.185.104.219 as permitted sender) client-ip=216.185.104.219;
Authentication-Results: mx.google.com;
       spf=softfail (google.com: domain of transitioning *** Email address is removed for privacy *** does not designate 216.185.104.219 as permitted sender) smtp.mail=*** Email address is removed for privacy ***;
       dmarc=fail (p=NONE dis=NONE) header.from=gmail.com
Received: (qmail 17818 invoked by uid 10040); 19 Oct 2013 07:56:30 +1100
Date: 19 Oct 2013 07:56:30 +1100
Message-ID: <*** Email address is removed for privacy ***>
To: *** Email address is removed for privacy ***
Subject: Test E-Mail #9 - 19/10/2013
X-PHP-Originating-Script: 10040:SCBTC_Send_Email_Example.php
From: *** Email address is removed for privacy ***
Reply-To: *** Email address is removed for privacy ***
X-Mailer: PHP/5.3.3
MIME-Version: 1.0
Content-Type: text/html; charset=ISO-8859-1

<font face="Arial" size="2" color="#000000">Test Message 9 with *** Email address is removed for privacy *** in safe senders list</font>

Using Google Mail (Webmail) to send to *** Email address is removed for privacy *** (Works without *** Email address is removed for privacy *** being in safe senders list)
------------------------------------------------------------------------------------------------------------------------------------------------------

x-store-info: sbevkl2QZR7OXo7WID5ZcV65/pkDWk7T3Fc8OPySipFXPRYXMNw5vR5UhTGHtB1evp1bf/L9N6Hob0jwxJbHTpF2Wbm6TvxWL9c6Rrk5cjCifR5kEvh2TgOJkzAQLZCUyVmMxubyYdA=
Authentication-Results: hotmail.com; spf=pass (sender IP is 209.85.215.49; identity alignment result is pass and alignment mode is relaxed) smtp.mailfrom=*** Email address is removed for privacy ***; dkim=pass (identity alignment result is pass and alignment mode is relaxed) header.d=gmail.com; x-hmca=pass header.id=*** Email address is removed for privacy ***
X-SID-PRA: *** Email address is removed for privacy ***
X-AUTH-Result: PASS
X-SID-Result: PASS
X-Message-Status: n:n
X-Message-Delivery: Vj0xLjE7dXM9MDtsPTA7YT0xO0Q9MTtHRD0xO1NDTD0w
X-Message-Info: gamVN+8Ez8V+RHg+F+brAVM6B0BP4EtWHv5DzG3W5QmkJE8NEFmYw9ASNMfH3NQLK+uh7e4UYxdH6NfTMjeXaCVhrvpSpjqOGB0gh+Ja+VhBGZPz8t3BxRbSpjXIB6+NPE1E7+GsVojXnZV8oN8qlWQuJvDNl7mvfBZvQOh1GAaRL31NbKBt2HQNeITPlsjvPfSsTDEhJAvZQgkQ9ytx8VjX8Y03QkxA
Received: from mail-la0-f49.google.com ([209.85.215.49]) by SNT0-MC2-F7.Snt0.hotmail.com with Microsoft SMTPSVC(6.0.3790.4900);
     Fri, 18 Oct 2013 11:50:38 -0700
Received: by mail-la0-f49.google.com with SMTP id ev20so1079920lab.36
        for <*** Email address is removed for privacy ***>; Fri, 18 Oct 2013 11:50:37 -0700 (PDT)
DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/relaxed;
        d=gmail.com; s=20120113;
        h=mime-version:date:message-id:subject:from:to:content-type;
        bh=rxXeZoTi5nG2smhRxZGNQ78Cj5J6d/spTq/zoFdxF3c=;
        b=Vkold4qJSKjGpMk5id8wXwOH15/HOZk2WWpzO7Aw5YeUVefxURW0NZJuePycSOqZeW
         Sk9rtEEVaa2B79SnL8k2cU/tHoMIj0aGJT5li7ChVlL/zFPlPytAeXhb9p4oVVEmkifT
         UYzszu7JTlS3i3e96q0EBhMOX6w95t/UyO2htQUAmbF8GsWUPEEl06Awh7vYQboIPc5H
         yPmx24fEk6+RMgetP5e2Mo+LQvTJjYk7K27SZNsqOXPxF+f5LkDT7s106ZOmiSrDBO0P
         fg9B1Khuc+/b74IZ39EkomGZ9+RzxUsOZrW4BLh5xQpWpnsyVj2Q5rLDp2/G+5pA2PRd
         3ilg==
MIME-Version: 1.0
X-Received: by 10.112.168.3 with SMTP id zs3mr3709758lbb.2.1382122237742; Fri,
 18 Oct 2013 11:50:37 -0700 (PDT)
Received: by 10.112.201.42 with HTTP; Fri, 18 Oct 2013 11:50:37 -0700 (PDT)
Date: Sat, 19 Oct 2013 04:50:37 +1000
Message-ID: <CAFJsNaz1qxS10Kh7nLTugKje8R79X6ERyE=*** Email address is removed for privacy ***>
Subject: Test E-Mail #1 - 19/10/2013
From: Ian Jope <*** Email address is removed for privacy ***>
To: *** Email address is removed for privacy ***
Content-Type: multipart/alternative; boundary=001a11c33fe60456bb04e90869f3
Return-Path: *** Email address is removed for privacy ***
X-OriginalArrivalTime: 18 Oct 2013 18:50:38.0787 (UTC) FILETIME=[F008E930:01CECC32]
X-SpamFlt-Status: Not Detected
X-KASFlt-Status: Lua profiles 51873 [Oct 17 2013]
X-KASFlt-Status: Version: 5.0.1
X-KASFlt-Status: Rate: 0
X-KASFlt-Status: Status: not_detected
X-KASFlt-Status: Method: none
X-SpamFlt-Phishing: Not Detected

Does anyone have any ideas as I am a volunteer Webmaster looking after a website for a local cycling club, and of which most people who use the site are technically illiterate and I don't want to explain to 30 members to put my e-mail address in the 'Safe Senders list' in Hotmail / Live / Outlook Webmail if I can avoid it.

Thanks, Ian Jope