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Email Header contains interanl Domain

Hyper V host contains:

1 DC
1 Exchange 2013

When you send email it sends it as server.domain.local
External DNS has an A record going to the IP setup as mx.domain.com
MX is the A record

I've checked the send connector and verified its sending out as mx.domain.com.  I'm fairly certain i've not checked something simple and that's whats causing this.  Right now the ultimate problem is we're being rejected at some hosts as spam despite having and SPF record...i'm thinking its because of what's mentioned above (plus, its just bad mojo to have that out in the world anyways).
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2 Solutions
Dave BaldwinFixer of ProblemsCommented:
Maybe but all the emails I get from Gmail also include the internal servers names and IPs.
i'm thinking its because of what's mentioned above (plus, its just bad mojo to have that out in the world anyways).
It's actually quite common and most likely not the cause of your issue. You mention that you have a DNS A record setup, but do you also have the reverse DNS PTR record setup for your public IP?

A quick way to test this is by running:
ping -a xxx.xxx.xxx.xxx

Open in new window

The output should be something like:
Pinging mx.domain.com [xxx.xxx.xxx.xxx] with 32 bytes of data...

Open in new window

If you don't see "mx.domain.com" after "Pinging", you'll need to get your ISP or network administrator to setup the reverse DNS PTR record.
THUMBTECHSAuthor Commented:
I would have them do that, however when I check the header its in the actual header itself...
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I would have them do that, however when I check the header its in the actual header itself...
This is the default behaviour of most mail systems and is totally acceptable. This would only really be a problem if your domain name is specifically blacklisted by the recipient's mail system.
Dave BaldwinFixer of ProblemsCommented:
Every mail server that the message goes thru is supposed to leave it's server name and/or address in your headers.  That is normal behavior.
THUMBTECHSAuthor Commented:
So, what you're saying is the below header is correct?

helocheck.abuseat.org rejected your message to the following email addresses:
helocheck@helocheck.abuseat.org (helocheck@helocheck.abuseat.org)
helocheck.abuseat.org gave this error:
*** The HELO for IP address 1xx.xxx.xx.xx was 'owa.xxxx.org' (valid syntax) ***
A problem occurred while delivering this message to this email address. Try sending this message again. If the problem continues, please contact your helpdesk.

Diagnostic information for administrators:
Generating server: xxxEX.xxx.local
helocheck.abuseat.org #550 *** The HELO for IP address 1xx.xxx.xx.xx was 'owa.xxxx.org' (valid syntax) *** ##
Original message headers:
Received: from xxxEX.xxx.local ( by xxxEX.xxx.local
 ( with Microsoft SMTP Server (TLS) id 15.0.516.32; Mon, 9 Sep
 2013 11:29:29 -0500
Received: from xxxEX.xxx.local ([::1]) by xxxEX.xxx.local ([::1]) with mapi id
 15.00.0516.029; Mon, 9 Sep 2013 11:29:29 -0500
From: THUMBTECHS Corporation <xxxxx@xxxxxx.org>
To: "helocheck@helocheck.abuseat.org" <helocheck@helocheck.abuseat.org>
Subject: test
Thread-Topic: test
Thread-Index: AQHOrXnBVhheZYKlj02TMOK2VmyBfA==
Date: Mon, 9 Sep 2013 16:29:28 +0000
Message-ID: <af5c7940257f4d15a3c75094bed1910f@xxxxEX.xxxx.local>
Accept-Language: en-US
Content-Language: en-US
x-originating-ip: [xxx.xxx.xxx.xx]
Content-Type: multipart/alternative;
MIME-Version: 1.0
Dave BaldwinFixer of ProblemsCommented:
The only thing I can see is that the remote server may be complaining that your domain address may not match your IP for some reason.  You can look up the responses for your domain here: http://www.mxtoolbox.com/

Yes the header looks fine for a standard Exchange setup.

Run this test against your server and let us know if there are any issues reported: http://www.mxtoolbox.com/diagnostic.aspx

From the above headers, it looks as though you've been setup with reverse DNS, which is good.

Have you had any bouncebacks since? If so, provide us with the exactly error message reported and we can help you out further.
THUMBTECHSAuthor Commented:

We are getting NDR's still:

Your message did not reach some or all of the intended recipients.

      Subject:    test
      Sent: 9/9/2013 8:36 AM

The following recipient(s) cannot be reached:

      'xxxxx@xxxxx.com' on 9/9/2013 8:37 AM
            Diagnostic code = SubmissionProhibited; Reason code = TransferFailed; Status code = 571
            <atl4mhib42.myregisteredsite.com #5.7.1 smtp;554 5.7.1 The message from (<rdaisyrobinson@fwbbb.org>) with the subject of (test) matches a profile the Internet community may consider spam. Please revise your message before resending.>
Dave BaldwinFixer of ProblemsCommented:
Yeh, don't send a message with 'test' for the subject.  I think that alone can get you bounced on some servers.  Yes, that is picky but it is their server and they can do what they want.  Send some kind of 'real' plain text message with at least two paragraphs.  If you were sending to Yahoo or Hotmail it still might bounce but they seem to do random rejections anyway.
As mentioned, try sending a legitimate email to the same recipient as above. It may just be that their spam filtering software has higher restrictions than normal.

It would be worth double checking that your mail server isn't any blacklists too. Use this tool to check your server's IP for blacklisting: http://www.mxtoolbox.com/blacklists.aspx
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