Exchange 2010 and custom transport rule

I am trying to create a transport rule that will reject the message with enhanced status code I created. Exchange doesn't seem to recognize the rule at all. I want to send a reply to anyone that sends an email to 1 of our old email domains that will no longer be available.

Rule
Apply rule to messages
from users that are "outside the organisation"  and when a recipients address matches "@olddomain.com"
send "Diags for email admins" to sender with '5.7.999"
I send test emails to myself with the old domain address, I get the emails but my google and yahoo accounts don't get an ndr
LVL 6
Smith and AndersenAsked:
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AmitIT ArchitectCommented:
Check Auto replies option is enabled at Org Level.

Check this
http://www.howto-outlook.com/howto/automaticreply.htm
Smith and AndersenAuthor Commented:
Hi Amit
I do have them all checked except for use message text line wrap at column
AmitIT ArchitectCommented:
Do you have any mailboxes or contacts for "@olddomain.com
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Smith and AndersenAuthor Commented:
Yes. My mailbox has an alias with the old domain address
AmitIT ArchitectCommented:
Test this, disable the rule and send email to that address and what is the result.
Smith and AndersenAuthor Commented:
Hi Amit
I disabled the rule and sent an email from my gmail account and I got the email
AmitIT ArchitectCommented:
Can you try this. Create a contact for that address and remove that address from mailbox. Then enable the rule and test again. Let me know the result. I did something similar long back, however I used mail marshal.
Smith and AndersenAuthor Commented:
Hi Amit
I figured out the issue
As soon as I made olddomain my primary address it worked
Can this be done for alias's??
AmitIT ArchitectCommented:
Good ...However, I haven't tired with Alias.
Will SzymkowskiSenior Solution ArchitectCommented:
Alias are not identified by rules in the Exchange environment. It will always use the Primary SMTP address which is why your test only worked when it was the Primary SMTP.

Will.
AmitIT ArchitectCommented:
I guess Will answers your question above. I suggest, creating contacts for old domain address and then set the rule.

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