Exchange 2007 on SBS 2008 clients cannot send to internal recipients using external email address?

I recently clean installed on of my clients SBS 2008 boxes as I had a problem with one of the hard disks and generally it needed a good clear out.

Since we are back up and the server is fully patched I am getting a strange thing where the clients when sending to each other used to use and this would get through to the internal mailboxes without problems.  Since the re-install if they do that they get an error like this:

"The recipient's e-mail address was not found in the recipient's e-mail system. Microsoft Exchange will not try to redeliver this message for you. Please check the e-mail address and try resending this message, or provide the following diagnostic text to your system administrator."

If the user's external email is if another user on the domain puts in just "Julie" as the To address it gets through, if they put "" they get the error above?

Is this some sort of DNS issue in Exchange or the SBS box? I ran the "Fix My Network" wizard and it identified that IPV6 wasn't configured on the network adapter and I fixed that but I can't imagine that would be the cause of the issue,  We also seem to be having an issue with autocomplete entries being remembered in a session where you create them and then being lost when you close out of Outlook could these two things be related?

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Nick RhodeIT DirectorCommented:
I am just assuming because that identical mailbox use to exist on the previous installation the cache/autocomplete is still referencing that specific mailbox even though they have the exact same address it is still searching for the old SBS server.  When typing the address in the To field and autocomplete box will pop-up with the address.  Simply delete it and then continue to type the full address and try it.

In short:

To: Julie

Is referencing the GAL so it knows where to send it to


Is probably in autocomplete referencing the old mailbox and needs to be removed.

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SivAuthor Commented:

I think you might have hit the nail on the head.  I was talking to my client who initially reported this and it does sound like the issue is something to do with the autocomplete list.

How does the autocomplete/suggested contacts  store the old server's version of the internal recipient that identifies it as not being the same as the current version of that user in the newly created GAL??

I thought it just held the address string which would be the same as it was before?

SivAuthor Commented:
I will chat with my clients this morning and get them to delete any autocomplete entries that point to internal addresses and then get them to manually type in and see if when they send internally the issue goes away. I'll post back here later.

SivAuthor Commented:

Sorry I forgot to get back to this page and award the points. Your solution was the fix for the problem. It seems the staff who were reporting issues were relying on the old auto complete entries when sending to local users on the network. Once the old auto completes where removed and the new ones created the issue went away.

Thanks again for your help.

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