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Email from sender cannot be rec3eived by one resipient, everyone else gets it.

I am running Exchange 2003.  I have a sender that when he sends an email to the President it bounces back But he can send to anyone else in our domain and it goes through.
The message he receives back is:  Unable to deliver message to the following recipients, due to being unable to connect successfully to the destination mail server.
In the details.txt file attachment this is the message:

Reporting-MTA: dns;Exchange.mydomain.com
Received-From-MTA: dns;mta4.srv.hcvlny.cv.net
Arrival-Date: Tue, 4 Oct 2011 14:40:52 -0500

Final-Recipient: rfc822;Shawn@mydomain.com
Action: failed
Status: 4.4.7
X-Display-Name: Shawn Smith

Have checked his Outlook for blocked sender.  Checked spam filter settings
Checked Message Tracking Center

SMTP: Message Delivered locally to Shawn@mydomain.com
SMTP: Message Scheduled to Retry Local Delivery
And this just keeps repeating.  If someone else is copied on it, they receive it in our domain

I'm scratching my head, anyone have any ideas?
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1 Solution
Are other recipients on the same server/LAN as the president?
It sure sounds like some type of security squashing it. 4.4.7 is a DELAY. Sometimes a delay means anti-virus or other security is dropping the connection because of a rule/filter.

What about the Exchange General > Delivery Restrictions on the president's user account? Anything there? Normally it should have from EVERYONE checked. Although, I think this scenario that cause an immediate bounce - not a 4.4.7 Delay.

DbarITAuthor Commented:
All our recipients are on the same LAN/Server
Message restrictions for him is set to accept messages From Everyone

What's really weird is that 1 message from the sender was delivered yesterday but everything else is bouncing around in the message Que
Sound like a bad entry in nk2 file or cached outlook address book.

Does it work from OWA?

If so, use nk2view from nirsoft http://www.nirsoft.net/utils/outlook_nk2_autocomplete.html to remove any entries for that recipient and rename sender's oab files and let them re download.

These oab files are in the same folder as the ost/pst by default for outlook 2003. userprofile\local settings applicationa data\microsoft\outlook\
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Linraf could have something... if sending to a legacy email address that doesn't exist any more it may sit in the queue doing a retry.
Anyway, this is easy to test. Have the sender manually select the president's name from the GAL by clicking on TO:. That should eliminate the Outlook cache. Or just type a partial name and do CHECK NAME.

Is it possible the President's email or alias changed?

I have had a manually typed email address still resolve to one from the outlook address book, and would still suggest the renaming of that oab files.
Sorry, I should have said that I have had the GAl that is cached in the oab files be the problem even after the entries are removed from the nk2.

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