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why are my messages from another domain being marked as spam when sent from gmail even though my gmail settings say to send from my server and I have confirmed the email address?

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why are my messages from another domain being marked as spam when sent from gmail even though my gmail settings say to send from my server and I have confirmed the email address? ummmidunno 4/30/12 11:13 AM
We have several people using gmail to send emails from our domain and they are all set up the same way, to use our outbound server to send.  The mail that we're sending from gmail is now getting rejected as spam because the emails are actually coming from gmail servers according to the non-delivery message as show below.  It was my understanding that the point of having that setting, "mail is sent through" was just to avoid this type of issue.  When I set up the account gmail confirmed the access worked (servername, port, user login and psw) so why isn't it being used?  


Delivery to the following recipient failed permanently:

     y...@yyyy.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: 552 552 4GDs1j00H3owFux01 :: auth :: Message rejected for spam or virus content :: Please include this entire message when contacting support :: v=2.0 cv=N7ur5hBB c=1 sm=1 p=uDHorEvhDXIA:10 a=2Hd6niVQWmpKLC2jWksA:9 a=wMgHoLLXa4qs3tQayRYA:7 a=wPNLvfGTeEIA:10 a=86plz6UFvS9zxqueSTQA:9 a=MfkF3ROADxZsb1arDkMA:7 a=FfkhIE2ZG45sUHoUpEKWUQ==:117 :: 100.00 (state 18).

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

MIME-Version: 1.0
Received: by 10.112.104.99 with SMTP id gd3mr8155892lbb.70.1335802432257; Mon,
 30 Apr 2012 09:13:52 -0700 (PDT)
Received: by 10.112.88.71 with HTTP; Mon, 30 Apr 2012 09:13:52 -0700 (PDT)
Date: Mon, 30 Apr 2012 09:13:52 -0700
Message-ID: <CAJbB5HBjW9GU1fkQuoEOH3xAyoR2bsVVwOnetOVbOiW5BG0vPg@mail.gmail.com>
Subject: Verify receipt of email please
From: Somebody <x...@xxxx.com>
To: Scarlett <y...@yyyy.com>
Content-Type: multipart/alternative; boundary=f46d0401680777001204bee7bd50

Re: why are my messages from another domain being marked as spam when sent from gmail even though my gmail settings say to send from my server and I have confirmed the email address? Joshua 4/30/12 11:34 AM
It looks to me like it is YOUR smtp server that is rejecting the message when gmail tries to hand it off. Can you check the settings on your server?
Re: why are my messages from another domain being marked as spam when sent from gmail even though my gmail settings say to send from my server and I have confirmed the email address? ummmidunno 4/30/12 12:29 PM
I didn't really want to put the person's email address in a public post but it is the destination address of where the email was supposed to be sent to that rejected it.  The problem is that GMAIL is sending the message and it shouldn't be from what I understand.  It should be logging into my smtp server to create and send the message and it is my smtp server that should then be sending it.

The specific settings I'm referring to are under accounts and import and they say myname <myn...@mydomain.com>
not an alias
mail is sent through: smtpout.secureserver.net
secured connection on port 465 using SSL

my understanding of the 'mail is sent through' setting is to have the mail be sent FROM my server.  In the above spam message you can clearly see that the receiver (which was the person to whom I'd sent the email from my 'myn...@mydomain.com' address) was rejecting a message it received from gmail and NOT from smtp.secureserver.net

My question is why is gmail trying to send the mail directly when the setting says to "send mail through"

 

Re: why are my messages from another domain being marked as spam when sent from gmail even though my gmail settings say to send from my server and I have confirmed the email address? Joshua 4/30/12 12:39 PM
In order to deliver email to the recipient site, gmail first gives it to its own smtp server, which then hands it off to your smtp server, which then hands it off to the recipient. I can't tell for sure, but it very well could be that first hand-off that is generating the error. Check with secureserver.net to see if they are filtering this mail.
Re: why are my messages from another domain being marked as spam when sent from gmail even though my gmail settings say to send from my server and I have confirmed the email address? ummmidunno 4/30/12 1:01 PM
Hi Joshua,

I think I'm not understanding something.  Why do I need to provide login credentials for the smtp server if gmail isn't actually sending from that server?  If gmail was actually logging into the server to send the email then the source in the non-delivery message would show up as secureserver.net rather than gmail.com or googlemail.com.  In fact, if I use a standard email client to send the mail (by logging into the server using the same credentials supplied in my gmail settings) then the email is received without and issue.  It's only when I'm sending from within gmail using that address that the email gets bounced.

Even stranger...i just received an email bounce FROM gmail for a mail that was sent from within gmail.  Can you help my set up my spf record so that when gmail sends email from my domain (as it is apparently doing) it will be delivered?  Details of the gmail rejected email that was sent FROM gmail are below:

Delivery to the following recipient failed permanently:


    coachr...@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: 552 552 4KTb1j00c3jmVAh01 :: auth :: Message rejected for spam or virus content :: Please include this entire message when contacting support :: v=2.0 cv=PKyNCIWC c=1 sm=1 p=uDHorEvhDXIA:10 a=DpYzLJQslbIA:10 a=ZfNCKGw_AAAA:8 a=4VL4HdPjyGoJGm2RFEwA:9 a=pS5Ap1dGtGHfgQRYHFsA:7 a=wPNLvfGTeEIA:10 a=6E0janzuNoQA:10 a=C7XLm0ndhKxQBh3d:21 a=7b1d7v9JyEAroZ12:21 a=d_zrvvH4pEsbdHvX0mcA:9 a=228ljECUZxHJ6vJ9WFMA:7 a=485kGrU91w0P3ryK8OMzug==:117 :: 100.00 (state 18).

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

MIME-Version: 1.0
Received: by 10.52.18.212 with SMTP id y20mr18933098vdd.50.1335814055582; Mon,
 30 Apr 2012 12:27:35 -0700 (PDT)
Received: by 10.52.166.39 with HTTP; Mon, 30 Apr 2012 12:27:35 -0700 (PDT)
Date: Mon, 30 Apr 2012 12:27:35 -0700
Message-ID: <CAKYMB1NzQVtnA6XC9dVHKV2MQN4iT9_Kwq7VBziFU2qLQmALvw@mail.gmail.com>
Subject: build new cancel system this week...details:
From: Julie Harris <ju...@myhreu.com>
To: Tim Harris <coachti...@gmail.com>
Cc: Julie Harris <coachjul...@gmail.com>,
       Ruschele Abbruzzese <coachr...@gmail.com>
Content-Type: multipart/alternative; boundary=bcaec501c10e44dd2d04beea72b1
 

Re: why are my messages from another domain being marked as spam when sent from gmail even though my gmail settings say to send from my server and I have confirmed the email address? Joshua 4/30/12 1:16 PM
When you submit a mail via the web interface, gmail needs to connect to your specified external smtp server. It does that by first handing off the mail to a google server, which then connects to that external smtp server (using your supplied credentials) to send. If everything goes well, the external smtp server accepts the mail and delivers it to the destination server. If there is a problem connecting to or sending through that external smtp server, google generates a bounce message like the one you see above.

The fact that you get a similar bounce when sending to a gmail address makes me pretty sure that the problem is with YOUR smtp server. The error message is coming from google and not from secureserver because google was unable to hand the mail off to secureserver because secureserver rejected it.


Re: why are my messages from another domain being marked as spam when sent from gmail even though my gmail settings say to send from my server and I have confirmed the email address? ummmidunno 4/30/12 5:27 PM
Josh,

Sorry, I'm definitely not understanding this.  The rejection message said it was rejected by the recipient domain, not my domain.  In the rejection above, that is gmail.com.  This issue all started when I added an spf record to my domain.  Since gmail wasn't supposed to be sending as my domain, I didn't add any google, gmail or mail.google domains to my spf records.  The fact that it was only after this change to the spf records that we started having problems tells me that the mail was never being send from my server and has always been sent directly from gmail just with the 'from' being my other domain.  So can you help me set up my spf records so that I can specifically allow mail being sent from gmail?  I just sent a test message directly using my email client logging into the same server that gmail has (smtpout.secureserver.net) and I was able to login and send the server without a bounce. When I sent a similar test message from within gmail, it showed up in my inbox immediately...implying to me that it never left gmail.

In any case, since it seems to be the addition of the spf record that started causing these issues, if you an provide guidance on how to set up gmail in my spf record, I would appreciate it.
Re: why are my messages from another domain being marked as spam when sent from gmail even though my gmail settings say to send from my server and I have confirmed the email address? Joshua 5/1/12 6:01 AM
The "recipient domain" thing is a little confusing. When using an external smtp server, the first "recipient domain" is actually that external server, not the final recipient domain.

I don't think monkeying with your spf records is going to fix anything. The issue seems to be that your smtp server is rejecting the mail that google tries to hand off to it for delivery. I'm pretty sure of that because I know that the message starting "552 552" is not a gmail error message. Since you got that message on a mail you sent from one gmail account to another, that makes me pretty sure that gmail is indeed trying to hand the mail to your smtp server and it is your smtp server that is having the problems.

To fix this, you should contact the tech support for your external smtp server. I don't think anything you can do from google's side (short of moving your domain to google apps) will fix this.
Re: why are my messages from another domain being marked as spam when sent from gmail even though my gmail settings say to send from my server and I have confirmed the email address? ummmidunno 5/1/12 9:28 AM
Joshua,

I think I fixed it.  As I said before, this only started happening when I added an SPF record for my domain.  It was NOT an issue with that external server (which is actually a godaddy email service).  It WAS because gmail was trying to send the mail directly rather than logging into the secureserver.net server to send the email as a client. Since this is how I normally send my emails (as I mentioned in posts above) and those sends were successful (whereas those being sent when logged into gmail from a browser were not) I knew that wasn't the issue.