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Unable to send emails to one single company using Exchange 2003/2007

Jerry Seinfield
Last Modified: 2013-12-09
Hi Experts,

We are running into some mail flow issues with unable to send emails to one single company. Just to clarify, we can receive email from same company, but not send emails. We also are fine sending/receiving emails to other companies without any issues

My organization as per below:

Mixed Exchange 2003/2007/2010 organization.

Symantec Outbound/inbound Scanners

Multiple Exchange 2003 bridehead servers

Multiple CAS/HUB 2007

Multiple CAS/HUB 2010

5 CCR 2007

Multiple exchange 2003 mailbox server

no edge servers

multiple external MX records for redundancy

Troubleshooting steps taken below with no luck:

1. Able to receive emails from companyx.com

2. Unable to send emails to companyx.com

3. Created a compliance rule on spam gateways to byspass any compliance rule and allow emails to companyx.com

4. companyx.com has checked their side and they are able to send/receive emails to/from any company, except for my company

5. Checked logs on outbound scanners, and got error below

too many timeouts resolving ‘companyX.com/MX’  (in  ‘.’ ?). disabling EDNS

6. Checked with MBXTools the external domain, and is all green, is not blacklisted

7. the external company is able to send/receive emails to/from other companies

8. Getting an NDRs as per below

From: Mail Delivery System [mailto:Mailer-Daemon@xxxx.companyX.com]
Sent: Sat, 2 Jun 2010 14:24:38 -0400
To: xxxxxxxxxxxxxxx
Subject: Undeliverable: xxxxxxxxxxxxxxxxxxxxxxxxx

Delivery has failed to these recipients or distribution lists:

An error occurred while trying to deliver this message to the recipient's e-mail address. Microsoft Exchange will not try to redeliver this message for you. Please try resending this message, or provide the following diagnostic text to your system administrator.

Diagnostic information for administrators:

Generating server: delivery

#< #5.0.0 smtp; 550 5.7.1 External client with IP address does not have permissions to submit to this server. Visit http://support.microsoft.com/kb/928123 for more information.> #SMTP#

Original message headers:

X-AuditID: 0a666446-b7bdfae000000a3b-4e-4c38b6368d0f
Received: from hubtransportserver.mycompany.com ( [x.x.x.x) by xxxxxxxxxxxxxxx (company x mail
 ) with SMTP id 7C.FB.02619.636B83C4; Sat, 2 Jun 2010 14:24:38 -0400
Received: from hubtransportserver.mycompany.com ([fe80::6884:8c14:57a6:a027]) by
 hubtransportserver.mycompany.com ([fe80::f9b5:81ad:6043:dcb%11]) with mapi; Sat, 2 Jun 2010 14:24:38 -0400
From: jack bauer <jackb@cmycompany.com>
To: "jhoss@companyx.com
Date: 2 Jun 2010 14:24:38 -0400
Subject: xxxxxxxxxxxxxxxxxxxxxxxxxxx
Thread-Topic: xxxxxxxxxxxxxxxxxxxxxxxxxxx
Thread-Index: AcsgWlQxEYrAmBydSpiOcVr6ROsyYw==
Message-ID: <FA3F097621672941959A98C5B91916E401FCC260@hubtransportserver.mycompany.com>
Accept-Language: en-US
Content-Language: en-US
x-cr-puzzleid: {593A2AE2-F555-4B42-9A09-AC0380A48079}
x-cr-hashedpuzzle: CMWJ FL3T JJpW Jj7V O8I0 PXaD gjgl s/od 0zGI 3W0l 7ExQ
 7K48 9GGe +jKb AAqKLQ==
 10 Jul 2010 18:04:24
acceptlanguage: en-US
Content-Type: multipart/alternative;
MIME-Version: 1.0
X-Brightmail-Tracker: AAAAAwAAAZEVExCnFRMnFg==

Can anyone point me on the right direction?

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