Send mail from Postfix to Exch

Exchange EDGE servers handle external SMTP feeds.
The RECEIVE Connectors / Network tab / lower section, shows IP addresses of server that can RELAY mail.
Make sure your server IP is added.

Hello,

I do not have Edge installed, just Exchange 2010.

Please advise.

Have a great day,

Don

To postmaster's point
You need to configure exchange's relay rules to allow the postfix system the rights to relay.

http://technet.microsoft.com/en-us/library/bb232021(v=exchg.141).aspx

Hello,

I followed the link and now I am getting:

Subject      Undeliverable: Test @ 837
From      Microsoft OutlookAdd contact
To      user@domain.netAdd contact
Date      Today 09:37
Delivery has failed to these recipients or groups:

"smtp:[winserv.domain.local]"@winserv.domain.local
A problem occurred and this message couldn't be delivered. Check to be sure the e-mail address is correct. If the problem continues, please contact your helpdesk.







Diagnostic information for administrators:

Generating server: winserv.domain.local

"smtp:[winserv.domain.local]"@winserv.domain.local
#554 5.4.4 SMTPSEND.DNS.MxLoopback; DNS records for this domain are configured in a loop ##rfc822;user@domain.com

Original message headers:

Received: from linserv.domain.local (192.168.217.20) by
 winserv.domain.local (192.168.217.10) with Microsoft SMTP Server id
 14.2.347.0; Wed, 6 Nov 2013 08:37:17 -0500
Received: by linserv.domain.local (Postfix)      id 39FB11F01C95; Wed,  6
 Nov 2013 03:38:26 -1000 (HAST)
Delivered-To: smtp:[winserv.domain.local]@linserv.domain.local
Received: from localhost (localhost.localdomain [127.0.0.1])      by
 linserv.domain.local (Postfix) with ESMTP id 30A9D1F005E6      for
 <user@domain.com>; Wed,  6 Nov 2013 03:38:26 -1000 (HAST)
X-Virus-Scanned: Debian amavisd-new at linserv.domain.local
Received: from linserv.domain.local ([127.0.0.1])      by localhost
 (linserv.domain.local [127.0.0.1]) (amavisd-new, port 10024)      with
 ESMTP id QHsufZK8c-4y for <user@domain.com>;      Wed,  6 Nov 2013 03:38:25
 -1000 (HAST)
Received: by linserv.domain.local (Postfix, from userid 33)      id
 870821F01C95; Wed,  6 Nov 2013 03:38:25 -1000 (HAST)
To: <user@domain.com>
Subject: Test @ 837
X-PHP-Originating-Script: 0:main.inc
MIME-Version: 1.0
Content-Type: text/plain; charset="UTF-8"; format=flowed
Content-Transfer-Encoding: 7bit
Date: Wed, 6 Nov 2013 09:38:25 -0400
From: <user@domain.net>
Message-ID: <66320439021c7c877db50c15d9fb5e1c@domain.net>
X-Sender: user@domain.net
User-Agent: Roundcube Webmail/0.7.2
Return-Path: user@domain.net
 Reporting-MTA: dns;winserv.domain.local
Received-From-MTA: dns;linserv.domain.local
Arrival-Date: Wed, 6 Nov 2013 13:37:17 +0000

Original-Recipient: rfc822;user@domain.com
Final-Recipient: rfc822;"smtp:[winserv.domain.local]"@winserv.domain.local
Action: failed
Status: 5.4.4
Diagnostic-Code: smtp;554 5.4.4 SMTPSEND.DNS.MxLoopback; DNS records for this domain are configured in a loop

Received: from linserv.domain.local (192.168.217.20) by
 winserv.domain.local (192.168.217.10) with Microsoft SMTP Server id
 14.2.347.0; Wed, 6 Nov 2013 08:37:17 -0500
Received: by linserv.domain.local (Postfix)      id 39FB11F01C95; Wed,  6
 Nov 2013 03:38:26 -1000 (HAST)
Delivered-To: smtp:[winserv.domain.local]@linserv.domain.local
Received: from localhost (localhost.localdomain [127.0.0.1])      by
 linserv.domain.local (Postfix) with ESMTP id 30A9D1F005E6      for
 <user@domain.com>; Wed,  6 Nov 2013 03:38:26 -1000 (HAST)
X-Virus-Scanned: Debian amavisd-new at linserv.domain.local
Received: from linserv.domain.local ([127.0.0.1])      by localhost
 (linserv.domain.local [127.0.0.1]) (amavisd-new, port 10024)      with
 ESMTP id QHsufZK8c-4y for <user@domain.com>;      Wed,  6 Nov 2013 03:38:25
 -1000 (HAST)
Received: by linserv.domain.local (Postfix, from userid 33)      id
 870821F01C95; Wed,  6 Nov 2013 03:38:25 -1000 (HAST)
To: <user@domain.com>
Subject: Test @ 837
X-PHP-Originating-Script: 0:main.inc
MIME-Version: 1.0
Content-Type: text/plain; charset="UTF-8"; format=flowed
Content-Transfer-Encoding: 7bit
Date: Wed, 6 Nov 2013 09:38:25 -0400
From: <user@domain.net>
Message-ID: <66320439021c7c877db50c15d9fb5e1c@domain.net>
X-Sender: user@domain.net
User-Agent: Roundcube Webmail/0.7.2
Return-Path: user@domain.net

Test @ 837

Please advise.  I know we are close!

Thanks for your help and have a great day,

Don

the error points to a configuration issue where your postfix mailing recipient is not identifiable by the MX/valid domain check on the exchange.

does "domain.net" exist?

on your exchange or postfix, nslookup -q=mx domain.net or dig domain.net MX respectively.

The domain check is an anti-spam method used to check whether the domain of a sender is valid (have an MX record or an A record for a server that will "point" to a possible server to which a bounce can be delivered.

Hello,

Doing either nslookup -q=mx domain.net or dig domain.net MX, they come up with:
mail.domain.net
winserv.domain.net

Should linserv.domain.net be added?

Thanks for your time and help,

Don

Your issue seems to be

"smtp:[winserv.domain.local]"@winserv.domain.local
#554 5.4.4 SMTPSEND.DNS.MxLoopback; DNS records for this domain are configured in a loop ##rfc822;user@domain.com

Suggests a misconfiguration seemingly leading to a loop.

not sure what this check is supposed to reflect/prevent.

I made some changes and getting a different message now:

Delivery has failed to these recipients or groups:
"smtp:[winserv.domain.local]"@winserv.domain.local
A problem occurred and this message couldn't be delivered. Check to be sure the e-mail address is correct. If the problem continues, please contact your helpdesk.
Diagnostic information for administrators:
Generating server: winserv.domain.local
"smtp:[winserv.domain.local]"@winserv.domain.local
#554 5.4.4 SMTPSEND.DNS.MxLoopback; DNS records for this domain are configured in a loop ##rfc822;user@domain.com
Original message headers:
Received: from linserv.domain.local (192.168.217.20) by
 winserv.domain.local (192.168.217.10) with Microsoft SMTP Server id
 14.2.347.0; Thu, 7 Nov 2013 00:16:43 -0500
Received: by linserv.domain.local (Postfix)      id BA4E41F01C9C; Thu,  7
 Nov 2013 00:17:12 -0500 (EST)
Delivered-To: smtp:[winserv.domain.local]@linserv.domain.local
Received: from localhost (localhost.localdomain [127.0.0.1])      by
 linserv.domain.local (Postfix) with ESMTP id AB29D1F01C79      for
 <user@domain.com>; Thu,  7 Nov 2013 00:17:12 -0500 (EST)
X-Virus-Scanned: Debian amavisd-new at linserv.domain.local
Received: from linserv.domain.local ([127.0.0.1])      by localhost
 (linserv.domain.local [127.0.0.1]) (amavisd-new, port 10024)      with
 ESMTP id YVEyATmHckUB for <user@domain.com>;      Thu,  7 Nov 2013 00:17:11
 -0500 (EST)
Received: from Laptop7 (c-68-58-136-101.hsd1.in.comcast.net
 [xxx.xxx.xxx.xxx])      (Authenticated sender: user@domain.net)      by
 linserv.domain.local (Postfix) with ESMTPA id B234B1F012E6      for
 <user@domain.com>; Thu,  7 Nov 2013 00:17:11 -0500 (EST)
From: Don <user@domain.net>
To: <user@domain.com>
Subject: Test @ 0016
Date: Thu, 7 Nov 2013 00:16:42 -0500
Message-ID: <00c701cedb78$8bb645e0$a322d1a0$@domain.net>
MIME-Version: 1.0
Content-Type: multipart/alternative;
      boundary="----=_NextPart_000_00C8_01CEDB4E.A2E14F50"
X-Mailer: Microsoft Outlook 14.0
Content-Language: en-us
Thread-Index: Ac7beIg28bLZ+Sf5R5eP76JAPPbfTg==
Return-Path: user@domain.net
Reporting-MTA: dns;winserv.domain.local
Received-From-MTA: dns;linserv.domain.local
Arrival-Date: Thu, 7 Nov 2013 05:16:43 +0000

Original-Recipient: rfc822;user@domain.com
Final-Recipient: rfc822;"smtp:[winserv.domain.local]"@winserv.domain.local
Action: failed
Status: 5.4.4
Diagnostic-Code: smtp;554 5.4.4 SMTPSEND.DNS.MxLoopback; DNS records for this domain are configured in a loop

Test @ 0016

Please advise.

Thanks for your help and have a great day,

Don

Do not use the same email address for both the sender and recipient.

This is likely a spam test which were/are common in an attempt to take advantage of people who white listed their own email address as not being spam source.

See if the issue exists when you mail from user1@domain.net to user@domain.net

on the linux/postfix system try the following:

echo "To: <user@domain.net>
From: <user1@domain.net>
Subject: test

this is a test
" | /usr/sbin/sendmail -oi -fuser1@domain.net -t

tail /var/log/maillog to see what happened to this message.  Was it delivered to the exchange server.

Then see what happens on the exchange side with the message.

Hello,

I am not using the same address for both.  I am using user@domain.NET as the sender and user@domain.COM as the recipient.

Please advise.

Have a great day,

Don

Are they pointing to the same mailbox on the exchange server?

I can only go based on the error you posted.

No, the .net account is on the Postfix server and the .com account is on Exchange.

Have a great day,

Don

your nslookup -q=mx information for domain.net points to winserv (exchange server) which might be why it is rejecting.

try any other domain for the sender and see what happens.

Hello,

I fixed the issue:

Diagnostic-Code: smtp;554 5.4.4 SMTPSEND.DNS.MxLoopback; DNS records for this domain are configured in a loop

In the main.cf file for Postfix, I had to change luser_relay = $user@servername.domain.local to luser_relay = $user@domain.local.

Now I am getting:

Delivery has failed to these recipients or groups:

"smtp:[winserv.domain.local]"@domain.local
 The e-mail address you entered couldn't be found. Please check the recipient's e-mail address and try to resend the message. If the problem continues, please contact your helpdesk.

Diagnostic information for administrators:

Generating server: winserv-1.domain.local

"smtp:[winserv.domain.local]"@domain.local
 #550 5.1.1 RESOLVER.ADR.RecipNotFound; not found ##rfc822;user@domain-1.com

Original message headers:
Received: from linserv.domain.local (192.168.217.20) by
 winserv-1.domain.local (192.168.217.11) with Microsoft SMTP Server id
 14.2.347.0; Fri, 8 Nov 2013 00:13:49 -0500
Received: by linserv.domain.local (Postfix)      id B02941F01C74; Fri,  8
 Nov 2013 00:14:18 -0500 (EST)
Delivered-To: smtp:[winserv.domain.local]@linserv.domain.local
Received: from localhost (localhost.localdomain [127.0.0.1])      by
 linserv.domain.local (Postfix) with ESMTP id 9F1CB1F01717      for
 <user@domain-1.com>; Fri,  8 Nov 2013 00:14:18 -0500 (EST)
X-Virus-Scanned: Debian amavisd-new at linserv.domain.local
Received: from linserv.domain.local ([127.0.0.1])      by localhost
 (linserv.domain.local [127.0.0.1]) (amavisd-new, port 10024)      with
 ESMTP id TlECf7ySqrw1 for <user@domain-1.com>;      Fri,  8 Nov 2013 00:14:04
 -0500 (EST)
Received: by linserv.domain.local (Postfix, from userid 33)      id
 8BCB71F01C74; Fri,  8 Nov 2013 00:14:04 -0500 (EST)
To: Donald Doyle <user@domain-1.com>
Subject: Test @ 0013
X-PHP-Originating-Script: 0:main.inc
MIME-Version: 1.0
Content-Type: text/plain; charset="UTF-8"; format=flowed
Content-Transfer-Encoding: 7bit
Date: Fri, 8 Nov 2013 01:14:04 -0400
From: <user@domain-2.net>
Message-ID: <ca441adcd97a396d6b3ef160fb8d7924@domain-2.net>
X-Sender: user@domain-2.net
User-Agent: Roundcube Webmail/0.7.2
Return-Path: user@domain-2.net

 
Reporting-MTA: dns;winserv-1.domain.local
Received-From-MTA: dns;linserv.domain.local
Arrival-Date: Fri, 8 Nov 2013 05:13:49 +0000

Original-Recipient: rfc822;user@domain-1.com
Final-Recipient: rfc822;"smtp:[winserv.domain.local]"@domain.local
Action: failed
Status: 5.1.1
Diagnostic-Code: smtp;550 5.1.1 RESOLVER.ADR.RecipNotFound; not found

Received: from linserv.domain.local (192.168.217.20) by
 winserv-1.domain.local (192.168.217.11) with Microsoft SMTP Server id
 14.2.347.0; Fri, 8 Nov 2013 00:13:49 -0500
Received: by linserv.domain.local (Postfix)      id B02941F01C74; Fri,  8
 Nov 2013 00:14:18 -0500 (EST)
Delivered-To: smtp:[winserv.domain.local]@linserv.domain.local
Received: from localhost (localhost.localdomain [127.0.0.1])      by
 linserv.domain.local (Postfix) with ESMTP id 9F1CB1F01717      for
 <user@domain-1.com>; Fri,  8 Nov 2013 00:14:18 -0500 (EST)
X-Virus-Scanned: Debian amavisd-new at linserv.domain.local
Received: from linserv.domain.local ([127.0.0.1])      by localhost
 (linserv.domain.local [127.0.0.1]) (amavisd-new, port 10024)      with
 ESMTP id TlECf7ySqrw1 for <user@domain-1.com>;      Fri,  8 Nov 2013 00:14:04
 -0500 (EST)
Received: by linserv.domain.local (Postfix, from userid 33)      id
 8BCB71F01C74; Fri,  8 Nov 2013 00:14:04 -0500 (EST)
To: User Name <user@domain-1.com>
Subject: Test @ 0013
X-PHP-Originating-Script: 0:main.inc
MIME-Version: 1.0
Content-Type: text/plain; charset="UTF-8"; format=flowed
Content-Transfer-Encoding: 7bit
Date: Fri, 8 Nov 2013 01:14:04 -0400
From: <user@domain-2.net>
Message-ID: <ca441adcd97a396d6b3ef160fb8d7924@domain-2.net>
X-Sender: user@domain-2.net
User-Agent: Roundcube Webmail/0.7.2
Return-Path: user@domain-2.net

Test @ 0013

Please note there are 2 Exchange servers involved in this, winserv & winserv-1.  My goal with these is for winserv to be the "main" server and winserv-1 act as a replication/failsafe server.

Sending a message to user@domain.local is received.  I do have the domain-1.com account setup under the user account AND it is receiving messages from outside the LAN.

Thank you and have a great day,

Don

The issue seems to be within the exchange server i.e. postfix submits/delivers the messages which are rejected.

Look at the exchange logs to see what is going on with the message in question.

Issue resolved!