Hello,
At work, we've set up a small Linux server with postfix on it, and configured 
postfix to use an external SMTP mail server. The related settings in main.cf:

myhostname = scm1.ourdomain.commydestination = scm1.ourdomain.com, 
localhostrelayhost = [externalmailer.ourdomain.com]
The external mail server is set up to trust internal connections, so there are 
no authentication or authorization constraints to worry about.
On the Linux server, if I use "telnet externalmailer.ourdomain.com 25", and 
then manually enter in a small email message to send email to an *EXTERNAL* 
email address (e.g. "b...@gmail.com") all the way from "HELO..." to "...QUIT", 
this works. The email is successfully received over at gmail.com.
However, if I (as user "s...@scm1.ourdomain.com") try to use "mail 
b...@gmail.com" from the Linux server, then this goes through the Postfix 
installation which in turn is configured to relay. However, this does not work 
ultimately. What happens:
1. The message is successfully delivered to the "externalmailer.ourdomain.com". 
I see this recorded in /var/log/mail.log.2. But a few seconds later, a message 
is delivered back to the sender on our Linux machine, and the relevant part of 
the error message is as follows:
Final-Recipient: rfc822;bob@gmail.comAction: failedStatus: 5.0.0Remote-MTA: 
smtp;MAILGW1.OURDOMAIN.COMDiagnostic-Code: X-Notes; Error transferring to 
MAILGW1.OURDOMAIN.COM;  Maximum hop count exceeded.  Message probably in a 
routing loop.
What I would like to ask is what is Postfix doing differently from me when I do 
a simple telnet to the external mail server? Why am I - by hand - able to send 
email via the relay, but Postfix is not? I know that I have misconfigured 
*something* ... but I can't figure out what.
I am attaching the full email message below.
Any help would be greatly appreciated!
Ahmed.
Return-Path: <>X-Original-To: scm@scm1.ourdomain.comDelivered-To: 
scm@scm1.ourdomain.comReceived: from mailgw.ourdomain.com 
(mailgw1.ourdomain.com [10.221.2.109])        by scm1.ourdomain.com (Postfix) 
with ESMTP id A7D1D440196        for <s...@scm1.ourdomain.com>; Fri, 17 Feb 
2012 22:09:52 +0300 (AST)X-AuditID: 
c74b5969-b7b85ae000001be8-92-4f3ea1446f3bReceived: from mail1.ourdomain.com 
(mail1.internal.ourdomain.com [10.221.2.110])        by mailgw.ourdomain.com 
(Symantec Messaging Gateway) with SMTP id 88.F0.07144.441AE3F4; Fri, 17 Feb 
2012 21:49:40 +0300 (AST)To: s...@scm1.ourdomain.com (SCM User)Subject: 
DELIVERY FAILURE: Error transferring to MAILGW1.OURDOMAIN.COM; Maximum hop 
count exceeded.  Message probably in a routing loop.X-Mailer: mail (GNU 
Mailutils 2.2)Date: Fri, 17 Feb 2012 22:09:46 +0300 (AST)From: 
postmas...@ourdomain.comx-MIMETrack: Itemize by SMTP Server on 
EXTERNALMAILER/OURDOMAIN(Release 7.0.3|September 26, 2007) at 02/17/2012 
10:09:34 PM,        Serialize b
 y Router on mail1/OURDOMAIN(Release 8.0.1|February 07, 2008) at 02/17/2012 
10:07:17 PM,        Serialize complete at 02/17/2012 10:07:17 PMMessage-ID: 
<of6dfeeb1b.0e59d703-on432579a7.00693efb-432579a7.00690...@ourdomain.com>MIME-Version:
 1.0Content-Type: multipart/report; report-type=delivery-status; 
boundary="==IFJRGLKFGIR14727182UHRUHIHD"X-Brightmail-Tracker: 
H4sIAAAAAAAAA+NgFnrFLMWRmVeSWpSXmKPExsXCdZcpT9dloZ2/waZd5hZ7W7uYHBg9Gr+8        
ZA5gjOKySUnNySxLJdK3S+DKuLTsGmvBed6KCT8PsjYwPuPuYuTjkBAwkWg5vY0FwhaTuHBv        
PVsXIxeHkMAFRok1v54xgSREBFQljnzaxAqSEBboZpSY8mwzI0SHkkTPvq9gNouAtsSxiSvY        
QWw2ATmJ5zevM4M0SAh0MklcfP0TyOHg4BUIldg/RQGkhldAUOLkzCdgm5kFUiVWTuhhm8DI        
MwtJahaS1CygbmYBdYn184QgwooSU7ofskPYqhKzdjWwQdgyEpundjKC2EIC1xglHu70hrCL        
Jc6cW846C+wdUYk3rTPAbGEBAYm751aAzYH5ZhaSb0DWsgGtPb3KcBayZ2YhPLOAkX8Vo0hu        
YmZOerledlpxRlGyXmpKqV5x4iZGYPwc947M3MHYdF37EKMAB6MSD++LTjt/IdbEsuLK3EOM        
EhzMSiK833KBQrwZVVqUX58UWlOanFhxiZODilGhj1mfpfLDH+z5K18ICQWtmVtLe
 7hC4E        
fnGcP1PL5NQU7SgVs4WR871Xq7xjnfHteyLX/ejlcyZc6vssbyUyceblJrae1FmyIs9/1d5z        
3r5y51qvpU2RazYs/PZo44eDs/+X+bh97Uq/G+nJeNpxZvDqC/ZTZ+45tt5zcdH0qqj7ByK/        
837f0GgjqsRSnJFoqMVcVJwIAFdMkpJ9AgAA
--==IFJRGLKFGIR14727182UHRUHIHDContent-Type: text/plain; 
charset=UTF-8Content-Transfer-Encoding: base64
WW91ciBtZXNzYWlDQoNCiAgU3ViamVjdDogVGVzdGluZw0KDQp3YXMgbm90IGRlbGl2ZXJlZCB0bzoNCg0KICBhaG1lZBzeXNjcy5jb20NCg0KYmVjYXVzZToNCg0KICBFcnJvciB0cmFuc2ZlcnJpbmcgdG8gTUFJTEdXM5LRlNIUkMuRURVLlNBOyBNYXhpbXVtIGhvcCBjb3VudCBleGNlZWRlZC4gIE1lc3NhZ2UgcHJvYmFibHkgaW4gYSByb3V0aW5nIGxvb3AuIA0KDQo=
--==IFJRGLKFGIR14727182UHRUHIHDContent-Type: message/delivery-status
Reporting-MTA: dns;mail1.ourdomain.com
Final-Recipient: rfc822;bob@gmail.comAction: failedStatus: 5.0.0Remote-MTA: 
smtp;MAILGW1.OURDOMAIN.COMDiagnostic-Code: X-Notes; Error transferring to 
MAILGW1.OURDOMAIN.COM  Maximum hop count exceeded.  Message probably in a 
routing loop.
--==IFJRGLKFGIR14727182UHRUHIHDContent-Type: message/rfc822
Received: from scm1.ourdomain.com ([10.248.200.233])          by 
externalmailer.ourdomain.com (Lotus Domino Release 7.0.3)          with ESMTP 
id 2012021722093403-158141 ;          Fri, 17 Feb 2012 22:09:34 +0300Received: 
by scm1.ourdomain.com (Postfix, from userid 1000)        id 42E45441F3B; Fri, 
17 Feb 2012 22:09:46 +0300 (AST)To: <b...@gmail.com>Subject: TestingX-Mailer: 
mail (GNU Mailutils 2.2)Date: Fri, 17 Feb 2012 22:09:46 +0300 (AST)From: 
s...@scm1.ourdomain.com (SCM User)X-MIMETrack: Itemize by SMTP Server on 
externalmailer/OURDOMAIN(Release 7.0.3|September 26, 2007) at 02/17/2012 
10:09:34 PM,        Serialize by Router on mail1/OURDOMAIN(Release 
8.0.1|February 07, 2008) at 02/17/2012 10:07:17 PM,        Serialize complete 
at 02/17/2012 10:07:17 PMMessage-ID: 
<of6dfeeb1b.0e59d703-on432579a7.00693efb-432579a7.00690...@ourdomain.com>

Testing

--==IFJRGLKFGIR14727182UHRUHIHD--
                                          

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