I've had a strange problem come up on my exchange 2003 server. I recently deleted an email account because they were no longer part of the organization. I went into the properties page of the new user and to the email addresses tab and added an additional smtp address. Problem is, when I send an email to the primary smtp address from the outside of the network, the email goes through fine. I also have sent an email to the secondary stmp address from outside the network and it rejects it with a 5.7.1 message that says that the user does not have permission to send mail to the account. I tried switching the secondary address and putting it as the primary address and I still had the problem. I turned on message tracking and did some further troubleshooting and found out that when I would send mail to that secondary address it was the intelligent message filtering (which I do have enabled) that keeps rejecting the message. I turned IMF off and the message went through fine. Why is is it that IMF rejects messages sent to the secondary address but it will allow message going to the primary address to go through fine without any problems. Here is an example of what I am talking about: lhenagan@mydomain.com - primary address mayor@mydomain.com- secondary smtp address added to email address tab in user properties All messages going to lhenagan@mydomain.com get through fine whereas mayor@mydomain.com will reject all messages. The only messages that mayor@mydomain.com will accept are from within the network domain. The old user was completely deleted from active directory so there shouldn't be any conflict. I also thought it could be some lingering object in AD so I did an exhaustive search and found nothing. IMF should apply rules equally to all email addresses and users throughout the domain. All settings for it are default and I didn't add any exceptions or anything that would cause this particular address not to receive mail. If someone can help me figure out this problem it sure would be appreciated! Thanks