Exchange 2007. Email Alias problems

I have SBS 2008 Server, with Exchange 2007. This issue involves three users.

They had accounts and email associated with the primary domain (mappingalaska.com). They also had alias account set up for a different domain, hosted elsewhere (gpsalaska.com). In short, they worked for two companies, but no longer work for the primary domain so their account were deleted. We still have users that work for the primary domain, with alias accounts to the outside domain.

The problem is that I receive NDR's when attempting to send mail to them. "#550 5.1.1 RESOLVER.ADR.RecipNotFound; not found ##". They can receive email if it originated form outside of the primary (mappingalaska.com) domain.

I have recreated the accounts on the primary (mappingalaska.com) domain and added the alias email address to their profiles. But they still don't receive the messages originating from the primary domain, but the NDR's have stopped. I have renamed the *.NK2 files in AppData, but that has not made a difference.

ideas?

Thanks.
mapalaska2003Asked:
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Miguel Angel Perez MuñozCommented:
I found some Outlook 2010 setup not uses nk2 files to keep users cache. Try on File menu > option > mail > click on Empty Auto-Complete List button.
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MAS (MVE)EE Solution GuideCommented:
1st option is to delete that entry from outlook cache and add as a new entry. Outlook see that as a different user which is not existing.
https://support.office.com/en-us/article/Delete-a-name-from-the-Auto-Complete-list-2e3d8fb1-eefd-4307-ab73-6f2f23164222?ui=en-US&rs=en-US&ad=US

2nd option is to convert the NDR to X500 and add it into the mailbox.
http://blog.westurn.net/2013/04/convert-ndr-to-legacyexchangedn-x500.html
https://support.microsoft.com/en-us/kb/2807779
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mapalaska2003Author Commented:
Thanks for the suggestions. I have eliminated the auto complete/cache, and the users are still not receiving my messages. When I reply to a message that they send, they do not receive the reply and I do not receive an NDR.
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Will SzymkowskiSenior Solution ArchitectCommented:
Have you checked message tracking after you have sent the email to this user? Is there anything in the Queues?

Will.
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mapalaska2003Author Commented:
I've checked message tracking. Interestingly, I am able to successfully send email to the recipients in question if I send the message from my alias (gpsaslaska.com) account. Just not from my domain (mappingalaska.com) account.
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MAS (MVE)EE Solution GuideCommented:
-->users are still not receiving my messages. When I reply to a message that they send, they do not receive the reply and I do not receive an NDR.

Your comment says u r receiving emails and you can reply.  Are you replying to the old emails received?
If possible please elaborate your issue.
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mapalaska2003Author Commented:
I have both my domain email and the other email (hosted outside) set yo for use in my Outlook. I can choose what account to send or replay to a message from. If I send it from the account that has the same domain name as the desired recipient, everything is fine. However f I try to send it from my domain account  to them, it does not ever leave my server. It just appears to disappear.
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David Johnson, CD, MVPOwnerCommented:
do you have a send connector?
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mapalaska2003Author Commented:
No I do not have a send connector
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David Johnson, CD, MVPOwnerCommented:
without a send connector you can't send outside of your organization
https://technet.microsoft.com/en-us/library/jj657457%28v=exchg.160%29.aspx?f=255&MSPPError=-2147217396
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mapalaska2003Author Commented:
Yes, I have a send connector set up. I can send messages to others that are not internal, Except to those that have local domain accounts that also have a secondary address (not bold-hosted by gmail, and are accessing their email remotely.

Here is what one of the profiles looks like. The bold address is withing our domain, and is on our internal Exchange 2007 server. The other is hosted outside of our organization. Mail messages created to send to the outside address, never reach the recipient and no NDR is generated. Basically, the message never actually leaves Exchange.
Mail-Properties.jpg
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David Johnson, CD, MVPOwnerCommented:
are you sending to or sending from? the items NOT in your organization have to have an account on the external email server and use that account.
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mapalaska2003Author Commented:
Sending to the account outside, from my organization. The outside account is hosted by google. The internal (domain) account is hosted on my local Exchange server.
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mapalaska2003Author Commented:
David--Thanks for your help with this. Deleting a bad entry in the DNS Settings, Forward Lookup Zones did the trick.

I really appreciate your help and expertise.
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mapalaska2003Author Commented:
Exceptionally knowledgeable and helpful.
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