We have a user who left the organization about a year ago. This users domain email account has been deleted for well over 9 months. When we try to send an e-mail to his personnal external e-mail account we get the following NDR telling us we were sending to his old Domain e-mail account Your message did not reach some or all of the intended recipients. Subject: Test from XXXXXXXXXXXXXXXXXXXX Sent: 7/27/2012 9:14 AM The following recipient(s) cannot be reached: User.Name@ourorg.com on 7/27/2012 9:14 AM The e-mail account does not exist at the organization this message was sent to. Check the e-mail address, or contact the recipient directly to find out the correct address. <mail.ourorg.com #5.1.1> We are running exchange 2003 SP2 with all updates. I have searched all of AD and this email address in not present anywhere. There are no contacts for him anywhere. Any clues to why this is happening would be greatly appreciated. Russ

Are you sure there isn't a personal contact in your outlook? Maybe nickname cache? When you start typing the external address and starts to auto complete click the delete button, then try sending again. Does his external email address also use the same convention user.name@externaladdress.com? James Chong MCITP | EA | EMA; MCSE | M+, S+ Security+, Project+, ITIL msexchangetips.blogspot.com

1. Do an ldifde dump of AD then open notepad do a search for both the internal and external address. ldifde -f export.ldf -s MYDC 2. Maybe someone registered a hidden event sink. http://msexchangetips.blogspot.com/2006/08/exchange-how-to-view-all-registered.htmlJames Chong MCITP | EA | EMA; MCSE | M+, S+ Security+, Project+, ITIL msexchangetips.blogspot.com

I did an export on all domains and neither address was found in the searches. I searched for all and even part of the addresses with no luck.Russ

I created the contact and set the external address and still get the same result. An NDR from his old internal address. We do not have another address in that domain we can send to Russ

I checked all the event sync's in the export and there not any. We did find out we can't send to this address from an external address either. However, this does not explain why we gat an NDR as if it was sent to an old Domain account and not an external account.Russ

what if you do a custom ldap search in AD proxyaddresses=smtp:emai@yourorg.com Does it return anything?Sukh

It does not return anything. I searched for both the Internal and external addresses just to be sure. I test the query with a good, known address just to be sure.Russ

Can you up the logging for SMTP& in particular the categoriser and see what the app log saysSukh

I checked all the event sync's in the export and there not any. We did find out we can't send to this address from an external address either. However, this does not explain why we gat an NDR as if it was sent to an old Domain account and not an external account. Russ Hello Russ, Just as I said before, this may he has sat his external account forward the emails to User.Name@ourorg.com. When you send email to his external account, it will redirect the emails to User.Name@ourorg.com, but the account (User.Name@ourorg.com)has been removed from your organization, so you get NDR for email to User.Name@ourorg.com. You can ask he go to check whether he has sat forward on his external account. Thanks, Evan Liu TechNet Subscriber Support in forum If you have any feedback on our support, please contacttngfb@microsoft.com Evan Liu TechNet Community Support

How about the issue, any updates? Thanks, Evan Liu TechNet Subscriber Support in forum If you have any feedback on our support, please contacttngfb@microsoft.com Evan Liu TechNet Community Support

If you cant send to this external account from another external then the issue is outside of exch and your env.Sukh

Glad the issue has been found now. Thanks, Evan Liu TechNet Subscriber Support in forum If you have any feedback on our support, please contacttngfb@microsoft.comEvan Liu TechNet Community Support