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5.5.0 smtp;550 Error when email is going to mulitiple recipients

Posted on 2006-06-19
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Last Modified: 2012-08-13
We are running Exchange Server 2003 SP2 and using Outlook 2002 as the client.  I have a user who cannot receive email from a particular sender, but only if she is one of several recipients of the same email.  In other words, if she is the only recipient she gets the email, but if she's part of a group of several recipients, the sender gets an error message that the email can't reach my user.

The error message that the sender gets is as follows:

There was an SMTP communication problem with the recipient's email server.  Please contact your system administrator.
<xxxx.org #5.5.0 smtp;550-mail.xxxx.org (xxxx.org) [IP address]: is currently not permitted>

I have many users who receive emails when they are part of a multiple recipient message with no problems, so I tend to think the problem lies with the sender's server.  Any suggestions as to what I can tell the sender to check for, if it is indeed their problem?

Thanks.
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Question by:dgbritt
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Exchgen earned 125 total points
ID: 16937407
Hello,

I am not too sure if this is a sender issue.... rather i feel its an issue at our end...

Looking at the NDR, "is currently not permitted" this protion tells me that the NDR was not generated by exchange. Do we have a firewall or spamfilter on or before exchange?

Something that does reverse query / spam database lookup etc.

Raghu
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by:dgbritt
ID: 16937473
Thanks for your reply.  Are your questions about firewalls and spam filter directed at the recipient's server (the one I administer), or the sender's?  

The recipient's email first goes through a PIX firewall and then through I Hate Spam for Exchange Server.  I Hate Spam does not reject email; it just sends it to our users' Spam-Quarantine folders in their Exchange mailbox account.

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by:Sembee
Sembee earned 125 total points
ID: 16938155
I don't think that NDR is an Exchange NDR. Exchange just isn't that polite. A quick Google on that error message throws it up coming from a number of sources, but no mentions of Exchange.
The problem is that you are the recipient. As such diagnosing the problem is close to impossible.
The first thing that needs to be clarified is what server is the message being delivered to. Is it yours or another one? Does the remote site use a smart host?

The NDR has their server in the message, so it is being generated at the initial handshake time, so the first server the message hits is generating the message.

Simon.
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