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We've setup a transport rule to catch mail sent to people that have left the company. We've then created Exchange contacts for the mailboxes that were closed and so we can refer to them from the rule using "people".

We even created a special DSN for our custom Enhanced Status Code and set the rule up so it'll use the special DSN code instead of the standard error message exchange returns. This works perfectly when sending email from outside of the domain. but when sending emails locally, a different error is given, and Exchange simply returned the misssing mailbox error.

Is there another way? something we've overlooked? the transport rule seem to be looking up an email address (user@domain formatted) while exchange and outlook clients use a different one?

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Can you post more about what filters and conditions you have included in your mail transport rule? Also can you ensure that when sending mail locally you are not using the auto-complete function in Outlook. –  Nic Young Feb 27 '12 at 5:50
    
Nic has a great point here. There's a possibility that the rule isn't triggering because the NK2 file has stored the legacy exchange address instead of SMTP. –  Chris N Feb 27 '12 at 12:26
    
Secondly, if an NDR triggers instead of this rule (because the accounts have been removed), it would be helpful for you to post that as well (with the sensitive bits generalized). –  Chris N Feb 27 '12 at 12:28
    
As @NicYoung suggested, it was the outlook auto-complete that tricked us. when removing the old contacts from the cache, sending an email produced the correct custom bounce message. –  Ereli Feb 28 '12 at 9:45

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Can you post more about what filters and conditions you have included in your mail transport rule? Also can you ensure that when sending mail locally you are not using the auto-complete function in Outlook

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I cant post the filters but i can confirm that the auto-complete was the issue. –  Ereli Feb 29 '12 at 9:21

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