exchange external email repeatedly blocked/undelivered

Hello, there is a specific email address that is being returned from everyone who uses exchange. What can i do about this, where could it be getting blocked
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mrbayItConnect With a Mentor Author Commented:
Delivery has failed to these recipients or groups:
A problem occurred during the delivery of this message to this e-mail address. Try sending this message again. If the problem continues, please contact your helpdesk.

Diagnostic information for administrators:

Generating server:
#< #5.0.0 X-Spam-&-Virus-Firewall; host[] said: 550-Please turn on SMTP Authentication in your mail client, or login to the 550-IMAP/POP3 server before sending your message. ( 550-[]:11275 is not permitted to relay through this server without 550 authentication. (in reply to RCPT TO command)> #SMTP#

Original message headers:

X-ASG-Debug-ID: 1358895570-03ba457845e8e700001-06K9AX
Received: from
 ( []) by with ESMTP id THieUuIF2DVpgvcL for
 <>; Tue, 22 Jan 2013 14:59:30 -0800 (PST)
Received: from ([::1]) by ([::1]) with mapi id 14.01.0218.012; Tue,
 22 Jan 2013 14:59:30 -0800
From: admin <>
X-Barracuda-Apparent-Source-IP: ::1
To: "''"
Thread-Index: Ac349CF0YdEiNX6FRFaJ8gKJEJm/ng==
Date: Tue, 22 Jan 2013 22:59:29 +0000
Message-ID: <>
Accept-Language: en-US
Content-Language: en-US
x-originating-ip: []
Content-Type: multipart/alternative;
MIME-Version: 1.0
X-Barracuda-Start-Time: 1358895570
X-Virus-Scanned: by bsmtpd at
X-Barracuda-Spam-Score: 1.30
X-Barracuda-Spam-Status: No, SCORE=1.30 using global scores of TAG_LEVEL=1000.0 QUARANTINE_LEVEL=1000.0 KILL_LEVEL=5.0 tests=HTML_MESSAGE, MISSING_SUBJECT, MISSING_SUBJECT_2
X-Barracuda-Spam-Report: Code version 3.2, rules version
      Rule breakdown below
       pts rule name              description
      ---- ---------------------- --------------------------------------------------
      0.00 HTML_MESSAGE           BODY: HTML included in message
      0.01 MISSING_SUBJECT        Missing Subject: header
      1.28 MISSING_SUBJECT_2      Missing Subject: header
You can check with your ISP first. Ask them to check the logs and see if they are blocking it at their router.
Can you post the bounce messages they get? What's the smtp error code you see on these bounces? Is this email being routed via a contact object in AD? From the email server, can you successfully query for the MX record for that domain, and telnet to that server on port 25?
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So people inside your organization are trying to send emails to, these emails are intended to go out your exchange server but then you get a hard bounce.

Do you have a specific send-connector on exchange for this domain?

What's interesting is that mx records for point to google (google apps, postini) but your exchange server is trying to connect to ( which requires to be authenticated before it allows you to send any email. Here's a test I did myself: ESMTP Exim 4.80 #2 Wed, 23 Jan 2013 13:07
14 -0800
220-We do not authorize the use of this system to transport unsolicited,
220 and/or bulk e-mail.
250 Hello [x.x.x.x]
mail from: <>
250 OK
rcpt to: <>
550-Please turn on SMTP Authentication in your mail client, or login to the
550-IMAP/POP3 server before sending your message.  (
550-[x.x.x.x]:44674 is not permitted to relay through this server without
550 authentication.

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can you do an nslookup as follows on your exchange server?

set type=mx

and show me what you get?
mrbayItAuthor Commented:
wow sir you are a true exchange admin. Thank you for your help thus far.

We have a barracuda spam filter that intercepts all traffic to deal with spam. i am not sure if we have a send connector for exchange, if you tell me how i can find out for you.

Here is what i got from that test you ask me to run

Non-authoritative answer:    MX preference = 20, mail exchanger = ALT1.ASPMX.L.GOOGLE
.com    MX preference = 30, mail exchanger = ALT2.ASPMX.L.GOOGLE
.com    MX preference = 10, mail exchanger =    MX preference = 40, mail exchanger = aspmx2.googlemail.c
om    MX preference = 50, mail exchanger = aspmx3.googlemail.c
mrbayItAuthor Commented:
any update sir?
Sorry for the delay,

Can you repeat your nslookup query without the 'server' line? Didn't mean to add it on my previous request.

set type=mx

Your barracuda seems fine, it's not the problem.

Did you inherit this system or did you set it up? Is the domain affiliated to your company at all?

On your Exchange Console, can you expand the Organization->Hub Transport, go to 'Send Connectors' and for every Connector you see on that tab, right click, go to properties, and go to 'address space'. See if any of them refer to or  or
mrbayItAuthor Commented:
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