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Email address rejected can't determine if isssue in internal or external?

I've got an Exchange 2007 server which forwards mail to an SMTP box and then to the end user's mail server. When I email an attachment (scanned PDF) to a particular person I keep getting messages kicked back.

Now I have no problems (to the best of my knowledge) with any other email address incoming or outgoing and the same thing goes for this end user.

My sending SMTP box is a Windows Web Server 2008 R2, and the receiving server is a Windows Small Business Server 2008 (w/ Exchange 2007).

Here is the bounce back message:

Delivery has failed to these recipients or distribution lists:

A communication failure occurred during the delivery of this message. Microsoft Exchange will not try to redeliver this message for you. Please try resending this message later, or provide the following diagnostic text to your system administrator.

Diagnostic information for administrators:

Generating server: mysmtpserver.company.local

#< #5.5.0 smtp;550 #5.1.0 Address rejected enduser@company.com> #SMTP#

Original message headers:

Received: from myexchangeserver.company.local ([x.x.x.4]) by
 mysmtpserver.company.local with Microsoft SMTPSVC(7.5.7600.16544); Fri, 11
 Jun 2010 13:21:40 -0400
Received: from mysmtpserver.company.local ([xxxx::xxxx:xxxx:xxxx:2788]) by mysmtpserver.company.local
 ([xxxx::xxxx:xxxx:xxxx:2788]) with mapi; Fri, 11 Jun 2010 13:21:39 -0400
From: "Lastname, My Firstname" <me@company.com>
To: "enduser@company.com" <enduser@sellmoreind.com>
Date: Fri, 11 Jun 2010 13:21:38 -0400
Subject: FW: Scan from copier
Thread-Topic: Scan from copier
Thread-Index: AcsJaxFcJ6O9fLZ1QoOCkChoDZsqBAAH2+Lg
Message-ID: <C7F018050EA4F2448D506EBE9EA232975DD0086BF0@myexchangeserver.company.local>
References: <chzYSyWaiETU7QlWaEf7qMOTO.1276267450.21@mycopier.company.local>
In-Reply-To: <chzYSyWaiETU7QlWaEf7qMOTO.1276267450.21@mycopier.company.local>
Accept-Language: en-US
Content-Language: en-US
X-MS-Has-Attach: yes
acceptlanguage: en-US
Content-Type: multipart/mixed;
MIME-Version: 1.0
Return-Path: me@company.com
X-OriginalArrivalTime: 11 Jun 2010 17:21:40.0167 (UTC) FILETIME=[8DF06570:01CB098A]

I'm also seeing this in my SMTP log on my SMTP server:

17:34:24 xx.xx.xxx.246 - - 0
17:34:24 xx.xx.xxx.246 EHLO - 0
17:34:24 xx.xx.xxx.246 - - 0
17:34:24 xx.xx.xxx.246 MAIL - 0
17:34:24 xx.xx.xxx.246 - - 0
17:34:24 xx.xx.xxx.246 RCPT - 0
17:34:25 xx.xx.xxx.246 - - 0
17:34:25 xx.xx.xxx.246 BDAT - 0

Any idea if this is something my SMTP is doing or the recieving Exchange box and it's SMTP service? GFI MailEssentials is installed on the recieving server but I don't even see my message show up in its logs so I don't think it's getting past the SMTP service...

Watch Question

Kyle AbrahamsSenior .Net Developer

This tells you it's your SMTP server:
Generating server: mysmtpserver.company.local

it's not liking the e-mail address for the user.  Perhaps you have the contact wrong in the scanners address book?
It looks like the problem was with my SMTP server. In the virtual server properties page under Advanced my FQDN was set to the internal DNS name of smtpserver.domain.local versus our external mail.company.com address. I change it and did an iisreset and it seems to have fixed the problem.