Question:

One of our clients is having an Entourage specific email issue. The issue only occurs when sending to a specific person (or perhaps the company/mail server). When an email is sent to this person, there is an immediate rejection notice as seen below:

Reporting-MTA: dns;<our domain>.com

Final-Recipient: rfc822;<recipient@recipient’s domain>.com
Action: failed
Status: 5.7.1
Diagnostic-Code: smtp;554 5.7.1 The message from (<sender@our domain.com>) with the subject of (<Subject>) matches a profile the Internet community may consider spam. Please revise your message before resending.
X-Display-Name: <Recipient’s Full Name>

(I edited out the domains, email addresses, and names)

This issue only happens when sending from Entourage. If I try sending from the same username in OWA it works fine. We are able to receive email from the recipient without any issues.

We have a forwarding rule and contact setup to forward emails to the recipients’ email address so that emails from recipient’s name@our domain.com is forwarded to the problematic recipient@recipient’s domain.com and if the Entourage user sends an email to the internal recipient’s name@our domain.com he gets the same rejection email, however the email is delivered to the local mailbox, just the forward to recipient@recipient’s domain.com fails.

Our email server is a Small Business Server 2003 Server running Exchange 2003. The user hasn’t reported any issues sending to other people. I do not know the recipient’s email provider, however the server listed for the MX record is inbound.registeredsite.com and the registrar is register.com The nameservers are from interland.net.

From my research I have found 2 posts regarding the same exact issue with no resolutions:

http://www.experts-exchange.com/Software/Server_Software/Email_Servers/Exchange/Q_21671954.html (the very last post after it was closed)

http://www.linkedin.com/answers/technology/information-technology/computers-software/TCH_ITS_CMP/394881-24898905 (The whole question)

I have not found any solutions, however there are some things I checked that people who have gotten a similar error not related to Entourage have done. I made sure the login from Entourage was secured using SSL (it already was), I tried sending an email in plain text (not HTML) format. Neither idea made any difference.

Entourage is connecting to Exchange directly (through OWA it appears), not through POP or IMAP. There don’t seem to be any issues with the connection to exchange.

Solution:

I’ve experimented with this a little and it seems that inbound.registeredsite.com blocks any email that has a “Received:” header already. So your culprit is the following header:

Received: from XXX.XXX.X.XXX *Client Mac’s Local IP Address* ([XXX.XXX.X.XXX]) *Client Mac’s Local IP Address* by clientserver.clientlocaldomain.local ([XXX.XXX.X.XXX]) *Client Server’s Local IP* with Microsoft Exchange Server HTTP-DAV ;
Mon, 16 Nov 2009 20:48:51 +0000

I think this is a misconfiguration on their server not yours.
I’ve looked around and it looks like Exchange 2007 allows you to strip internal “Received:” headers but I could not find a way to do the same on Exchange 2003.

http://social.technet.microsoft.com/forums/en-US/exchangesvradmin/thread/53472c36-4324-4852-9d63-411a287f3ef5/