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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.

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Chris, to clearify. This only happens when you are sending from an @gmail.com email in your @offby1.net Google Apps email. You are not getting any rejections from @offby1.net. If you have any additional info let me know and I'll do my best to help. My one suggestion at this point is to add all the mx records for Google. google.com/support/a/bin/answer.py?answer=174125 –  citadelgrad Aug 5 '10 at 18:47
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6 Answers

up vote 3 down vote accepted
+50

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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I would recommend changing your password - if your account has been hacked (and then flagged by Google as a possible spam source) they sometimes will bounce your outgoing email. Changing your password "should" clear the flag - at least it did the one time I had this problem on one of my accounts.

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Perhaps you changed your password for Apps or GMail and have not updated this in other configurations you are using.

I'd suggest you look at the Google Support Forums on this topic for additional possibilities, but that looks like slim pickings.

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1  
There's no password in play here; I'm sending my email from the google apps web mail interface, to a gmail account. How on earth could my password be an issue? –  Chris R Aug 1 '10 at 18:44
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If your email is relaying from a non-gmail server, then your gmail.com return address may be failing SPF-type (gmail.com does not appear to have specific SFP records set up) checks.

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Please elaborate; I'm not at any point in this dealing with a mail server that isn't owned by Google; I'm using the web interface to my google apps email, sending from an apps account to a vanilla Gmail account. –  Chris R Aug 1 '10 at 18:45
    
In that case, it's probably a Google support situation. Have you contacted Google? –  user48838 Aug 1 '10 at 19:19
    
How does one manage that? Google is pretty opaque when it comes to supporting their free offerings. –  Chris R Aug 2 '10 at 1:45
    
Don't know, that's why there is a growing anti-Google push. It's "free" and you get what you pay for, but it's not really "free" when you factor in what they collect against what they may or may not do with the collected information... –  user48838 Aug 2 '10 at 1:49
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Try this Email Server Test. It will tell possible reasons your emails could be getting bounced.

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Has your offby1.net been black listed somehow? It may be worth checking.

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