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Exchange 2010 relays from external website 550 SPAM EMAIL NOT ACCEPTED

Posted on 2013-01-03
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Last Modified: 2013-01-04
Hi,

We have a requirement from a client to set their Exchange (2010/SBS2011) to allow their externally-hosted website to relay using authentication.

For testing purposes I've created a new Receive Connector and specified it with my IP address and Basic Authentication.  If I now use telnet to connect I can authenticate fine, however when I try to send an email I get '550 ######## SPAM EMAIL NOT ACCEPTED ########'.  It's my understanding that authenticated connections automatically bypass the Exchange AntiSpam filters and so this shouldn't happen, so I'm confused as to what's going on.  

The full telnet connection transcript is as follows:

220 *** Microsoft ESMTP MAIL Service ready at Wed, 2 Jan 2013
 17:31:17 +0000
ehlo
250-*** Hello [***]
250-SIZE 10485760
250-DSN
250 AUTH LOGIN
auth login
334 VXNlcm5hbWU6
*** UGFzc3dvcmQ6
*** 2.7.0 Authentication successful
mail from: ***
250 2.1.0 Sender OK
rcpt to: ***
250 2.1.5 Recipient OK
data
354 Start mail input; end with <CRLF>.<CRLF>
test
.
550 ######## SPAM EMAIL NOT ACCEPTED ########

I also tried allowing anonymous connections on that receive connector, then running the PowerShell command to set anonymous connections to bypass the Exhange AntiSpam filters, but I get the same issue.

Any help much appreciated.

KP57610
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Question by:mtxit
4 Comments
 
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Accepted Solution

by:
caronas earned 250 total points
ID: 38739734
Your test is wrong. Dit you try a real mail?

SMTP-Mail is like this test:
data
Subject: This is a test mail

This is the ascii mail-body. The empty newline above must be there for splitting header from mail-body. The mail must end with a singe line with only a dot in it.
.

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Try this. If the error occurs again perhaps your Firewall or Exchange-Anti-Spam-Filters react on your input. Perhaps there is an attachment in the real mail that is not allowed or the headers or body is declared as spam. Check your Firewall maillog and the application eventlog on Exchange-Server for Spam-Informations. You can enable logging on your (used) Incoming Connector and look in the logs in your Exchange-Installation-Folders (Transport -> SmtpLogs)
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Expert Comment

by:Amit
ID: 38739879
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LVL 63

Assisted Solution

by:Simon Butler (Sembee)
Simon Butler (Sembee) earned 250 total points
ID: 38739902
The error that you have posted is NOT an Exchange NDR. It is being generated by something else. I would suspect AV or Antispam software installed on the server itself is rejecting the email. You will need to look at the software configuration to see if the server can be excluded from the scanning.

Simon.
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Author Closing Comment

by:mtxit
ID: 38743682
Thanks caronas and Sembee2, it turned out to be a combination of two issues - I wasn't formatting the email correctly within telnet, and a third-party anti-spam filter (Exclaimer Anti-Spam) was rejecting the mails.
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