Google Apps Email Bounce – Common Causes

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I have started to get Delivery Status Notification (Failure) messages in response to emails sent from my Google Apps domain account (at offby1.net):

Delivery to the following recipient failed permanently:

    **obfuscated**@gmail.com

Technical details of permanent failure:
Google tried to deliver your message, but it was rejected by the recipient domain. We recommend contacting the other email provider for further information about the cause of this error. The error that the other server returned was: 535 SMTP AUTH failed with the remote server. (state 8).

----- Original message -----

MIME-Version: 1.0
Received: by 10.231.15.68 with SMTP id j4mr4287274iba.184.1280629657624; Sat,
       31 Jul 2010 19:27:37 -0700 (PDT)
Received: by 10.231.145.136 with HTTP; Sat, 31 Jul 2010 19:27:37 -0700 (PDT)
X-Originating-IP: [174.3.246.112]
In-Reply-To: <AANLkTik3P7NjrT=sx77qe53z7=xMN1rHjk73iNjQkXsg@mail.gmail.com>
References: <AANLkTim4GVg12AufTZOPaqvY-i-N86ey-3bCjCKk+74v@mail.gmail.com>
       <AANLkTik3P7NjrT=sx77qe53z7=xMN1rHjk73iNjQkXsg@mail.gmail.com>
Date: Sat, 31 Jul 2010 20:27:37 -0600
Message-ID: <AANLkTinbytgETeTnD+Qi6Fs_40aXwmuHj4KC0tYvoaRv@mail.gmail.com>
Subject: Re: favour
From: Chris Rose <**alias**@gmail.com>
To: ************* <**obfuscated**@gmail.com>
Content-Type: text/plain; charset=ISO-8859-1
Content-Transfer-Encoding: quoted-printable

No prob. Hope it all comes together.

On Sat, Jul 31, 2010 at 11:23 AM, Victoria Bass <**obfuscated**@gmail.com> wrote:
> hey chris-
> thanks so much for registering my courses! i worked out the kinks so no
> worries. i really appreciate it.
> thanks again!
> cheers!

I'm sending messages to various ISPs; not just gmail. The only thing that might be an issue is that the from: address is my old gmail account address, which forwards to my apps account at offby1.net.

What is causing this? How can I stop it? This has been going on for about four days now, and it's happened once before, but I never was able to ascertain why.

Update

Because it probably bears on this, I am not using an SMTP server of my own, nor in fact am I sending this using an email client on my desktop. I'm using the Google Apps webmail client to send this, so if there's an SMTP server configuration at issue, it's nothing I've got any control over — that I know of.

Best Answer

First add SPF record to your DNS zones

offby1.net.    IN      TXT "v=spf1 a mx include:aspmx.googlemail.com _spf.google.com ~all"

It basically says that google apps is sending email on behalf of offby1.net.

Also add this to your MX records (from a short inspection it seems you don't have all the MX records).

offby1.net.    14400   IN      MX      10      ASPMX.L.GOOGLE.COM.
offby1.net.    14400   IN      MX      20      ALT1.ASPMX.L.GOOGLE.COM.
offby1.net.    14400   IN      MX      20      ALT2.ASPMX.L.GOOGLE.COM.
offby1.net.    14400   IN      MX      30      ASPMX2.GOOGLEMAIL.COM.
offby1.net.    14400   IN      MX      30      ASPMX3.GOOGLEMAIL.COM.
offby1.net.    14400   IN      MX      30      ASPMX4.GOOGLEMAIL.COM.
offby1.net.    14400   IN      MX      30      ASPMX5.GOOGLEMAIL.COM.

Then I would go and search RBL database, and find out if your domain/IP has been blacklisted.

A quick check show that your domain is listed: http://www.mxtoolbox.com/SuperTool.aspx?action=blacklist%3aoffby1.net

It's possible that your IP is listed there because this IP isn't supposed to send mails (that usually happen with entire IP class of certain ISP or hosting companies, and you're required to send a request on that RBL to add that IP as an authorized IP to send email).

Hope it helped.

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