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Email Bounce

Thank you for reading my question.

Environment:

Box 1 - Windows Server 2003 Domain Controller (Windows 2003 Domain/Forest)
Box 2 - Windows Server 2008 x64 - Exchange 2007 STD server (Not a domain controller)

I have one user who had an issue receiving email, long story short, we ended up giving her an entire new mailbox.  This is not the issue at hand however.  The user's old mailbox was renamed and is essentially dead.  The user has been using the new mailbox (same email address - the old box's email address was changes to jsmith42@domain.com) for sometime.  There are a handful of external people who when they email are receiving a bounce back from the jsmith42@domain.com.  So I'm confused.

First, why are emails being directed to that old email address?  Second, I have the old account enabled and forwarding mail to the new address, why isn't it making it to the new mailbox?

I have confirmed mail from multiple external and internal sources with the correct jsmith@domain.com all get to the location as intended.  I had originally thought it was a caching issue, but since multiple senders are involved I don't believe that is the issue.

The actual bounce back message:

****************************Message **********************************

From: Postmaster [mailto:postmaster@senderdomain.com]
Sent: Friday, March 16, 2012 7:48 AM
To: Joe Sender
Subject: [Postmaster] Email Delivery Failure

This is a delivery failure notification message indicating that an email you addressed to email address :
-- jsmith42@domain.com

could not be delivered. The problem appears to be :
-- Recipient email address is possibly incorrect

Additional information follows :
-- 553 sorry, no mailbox here by that name. ulc: 6754727891, rcp: 0001. (#5.7.1)

This condition occurred after 1 attempt(s) to deliver over a period of 0 hour(s).

If you sent the email to multiple recipients, you will receive one of these messages for each one which failed delivery, otherwise they have been sent.

****************************Message **********************************

Could this be an X500 issue?  I thought that was only used as an internal protocol either between mailboxes or between email servers on the same domain.

Any and all assistance would be greatly appreciated.
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ThirdEyeTech
Asked:
ThirdEyeTech
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2 Solutions
 
kollenhCommented:
Do you just have the one Exchange server, hosting all the roles?  Is there anything else that touches your mail system such as spam management, AV filtering, etc.?

I would try manually testing mail delivery to the 'jsmith24@domain.com' address by using telnet:
telnet {internet-mail-relay-address} 25
ehlo domain.com
mail from: user@domain.com
rcpt to: jsmith24@domain.com

If the last command comes back with a 553 error message then you know why messages are bouncing - your mail gateway doesn't know it's a valid mailbox.

My initial thought on your problem is that you have a conflicting setting between the two mailboxes.  It may take some digging to find, hopefully I can help.
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ThirdEyeTechAuthor Commented:
Kollenh,

Thank you for your response.  I completely forgot about the hosted SPAM filter.  I just added an alias and all was received fine.  Do you have any idea why the senders would be sending to jsmith42@domain.com instead of just jsmith@domain.com?
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kollenhCommented:
My first thought on that is the person sent an email and the (wrong) reply-to address was tagged on the outgoing message.  Perhaps during the time you were moving addresses around?
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ThirdEyeTechAuthor Commented:
Your advice worked.  Thank you for assistance.
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