My company provides private research tools (sites) for companies. Each site has its own domain name and users. These sites need to be able to send outbound mail for notifications such as password reminders. We started using Google Apps for this purpose, but lately we are having tremendous problems with mailing, especially to hotmail.

I added the SPF record as required. Mxtoolbox says my domains are not in any blacklists.

I was told to contact https://postmaster.live.com/snds/addnetwork.aspx and add my network. Given that I am using google's mail servers for sending mail, should I add their IP address for registering my domain? Or should I add my server's IP even though I am not hosting the mail server on it?

Here's an example of a returned message;

> Delivered-To: info@achbanlek.com Received: by with SMTP
> id 3csp62757lbo;
>         Mon, 10 Dec 2012 10:42:55 -0800 (PST) DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/relaxed;
>         d=gmail.com; s=20120113;
>         h=mime-version:from:to:x-failed-recipients:subject:message-id:date
>          :content-type;
>         bh=x41JiCH75hsonh+5c/kzwIs7R8u4Hum2u396lkV3g2w=;
>         b=v+bBPvufqfVkNz2UrnhyyoGj1Cuwf6x/yMj0IXJgH27uJU7TqBOvbwnNHf33sQ7B9T
>          uGzxwryC2fmxBh72cGz1spwWK348nUp6KK73MXKnF8mpc3nPQ8Ke+EQpSPeJdq/7oZvd
>          scZTGpy//IiGEUDU5bJ7YPqYXQRycY5N6AF5iI4mWWwbS4opybp3IKpDDktu11p/YEEO
>          Fj9wnSCx3nLMXB/XZgSjjmnaluGhYNdh3JFtz83Vmr50qXTG/TuIXlkirP73GfGvIt2S
>          7sy8/YdEbZR92mYe9wucditYr7MOuyjyYrZYCg+weXeTZiJX1PfBVieD+kD9MnCairnP
>          rQeQ== Received: by with SMTP id e45mr52766237eep.0.1355164974784;
>         Mon, 10 Dec 2012 10:42:54 -0800 (PST) MIME-Version: 1.0 Return-Path: <> Received: by with SMTP id
> e45mr65950764eep.0; Mon, 10 Dec 2012  10:42:54 -0800 (PST) From: Mail
> Delivery Subsystem <mailer-daemon@googlemail.com> To:
> info@achbanlek.com X-Failed-Recipients: ********@hotmail.fr
> Subject: Delivery Status Notification (Failure) Message-ID:
> <047d7b603d18ef1de304d083ee38@google.com> Date: Mon, 10 Dec 2012
> 18:42:54 +0000 Content-Type: text/plain; charset=ISO-8859-1
> Delivery to the following recipient failed permanently:
>      *********@hotmail.fr
> Technical details of permanent failure:  Message rejected.  See
> http://support.google.com/mail/bin/answer.py?answer=69585 for more
> information.
> ----- Original message -----
> Received: by with SMTP id
> e45mr52766228eep.0.1355164974700;
>         Mon, 10 Dec 2012 10:42:54 -0800 (PST) Return-Path: <info@achbanlek.com> Received: from WIN-1BBHFMJGUGS ([])
>         by mx.google.com with ESMTPS id l3sm26787704eem.14.2012.
>         (version=TLSv1/SSLv3 cipher=OTHER);
>         Mon, 10 Dec 2012 10:42:54 -0800 (PST) Message-ID: <50c62d2e.83b50e0a.19fb.fffff9ff@mx.google.com> MIME-Version: 1.0
> From: info@achbanlek.com To: *********@hotmail.fr Date: Mon, 10 Dec
> 2012 10:42:54 -0800 (PST) Subject: Rejoignez-nous sur achbanlek.com
> Content-Type: text/html; charset=utf-8 Content-Transfer-Encoding:
> base64
> ----- End of message -----

Your message is being rejected by Google, not by Hotmail. Google rejects outbound messages that it judges to be spammy. Google Apps is not meant to be used as a generic SMTP relay, even for legitimate mail.

All you can do in this situation is change your usage pattern to one that doesn't look spammy (unlikely if you are sending similar notifications to large numbers of users) or change to a different SMTP relay solution.

If you are not interested in operating your own SMTP server, you need to start working with a legitimate outbound E-mail service. Examples include AuthSMTP and Amazon SES.

  • +1, this is not what Google Apps is designed to be used for. – ceejayoz Dec 10 '12 at 19:37
  • I have switched to Amazon SES for automated mails, thank you for showing the right direction. – detay Dec 11 '12 at 5:55

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