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Fix a problem with SMTP and Exchange SBS 2003: 550 Administrative Prohibition

Posted on 2008-11-19
Medium Priority
Last Modified: 2012-05-05
I am having problems with email bouncing Back on one of our email addresses.

We are running Exchange on SBS 2003 and (as far as I can tell) Have smart hosts properly configured.

I have checked that the domain is not blacklisted and I can send email internally as well as from other addresses on the same domain through the same gateway.  The problem only exists on the email address/user account.

When I checked the Message Tracking Center in Exchange System Manger for the test emails I found that the SMTP Transfer was started and then immediately a Non-Delivered Report was Generated.

I have also Managed to use telnet to send a message through our SMTP server as that email address.

I'm Stumped.  Can anyone in the cloud figure it out?

Attached is the bounce back reply.
Your message did not reach some or all of the intended recipients.
      Subject:	test
      Sent:	11/18/2008 1:51 PM
The following recipient(s) could not be reached:
      [user]@Hotmail.com on 11/18/2008 1:51 PM
            There was a SMTP communication problem with the recipient's email server.  Please contact your system administrator.
            <[mydomain].com #5.5.0 smtp;550 Administrative prohibition>

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Question by:b00meRr
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LVL 33

Expert Comment

ID: 23007725
Have you read this link  http://support.microsoft.com/kb/300171 ??


Author Comment

ID: 23035627
As I said, the problem only exists on the one user account.  So it probably isn't a reverse dns issue.
LVL 33

Expert Comment

ID: 23040285
It's just a troubleshooting step - would you mind checking it.

Else, disconnect the user account - create a new mailbox and check if it works - if it does export messages from old mailbox to new one.

If it doesn't "it is not a problem with one user"

Accepted Solution

b00meRr earned 0 total points
ID: 23041623
As it turns out, you have to make sure that the correct email address is selected as primary in the Active Directory user settings.  After I did this the email worked flawlessly.

Author Comment

ID: 23041649
To be specific.

You need to select the correct SMTP email address.  It turns out that the incorrect SMTP email address was selected as primary and as a result our email provider was bouncing back the messages.

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