Outlook:  your message did not reach some or all of the intended recipients

SupermanTB
SupermanTB used Ask the Experts™
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I've got a user with Outlook 2003 SP3 that is experiencing the error described below.  This issue only occurs when the user emails this particular email address.  I've tried switching outgoing mail servers from the ISP's outgoing mail server to the email hosting service's outgoing mail server and the user still has this problem.  I also recently changed the email hosting to another service and now and using their outgoing mail server and the problem is still happening.  The user is able to email that address from the GoDaddy webmail interface.

My guess is that it doesn't appear to be a Outgoing mail server issue.  Also of interest, when I send the email it immediately pops into the Inbox as undeliverable.  It's so fast that it doesn't feel like it has had time even to leave the computer.

I've seen issues online where Outlook causes that problem, but they all appear to be related to Outlook 2003 SP1.  I've done all the updates on this computer, so I don't think that's an issue.

Outlook is configured with Exchange to store the email data, although the email is not hosted with Exchange.  They have a GoDaddy POP account configured to check their email.

Your message did not reach some or all of the intended recipients.

      Subject:             test3
      Sent:                 7/21/2009 9:23 AM

The following recipient(s) could not be reached:

      Diane & Stewart (xxxx@earthlink.net) on 7/21/2009 9:23 AM
            None of your e-mail accounts could send to this recipient.

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this problem is due to the corrupt cache address book .. try deleting the .nk2 files . this should help you out

Author

Commented:
Will that delete the autofill addresses?  I only ask because this particular user is unbelievably sensitive about change to their computer.  
yes it will delete the autofill address.. i think you have to delete orelse the user wil have no ways to get rif of this prob
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Author

Commented:
I'm assuming I can save these files and then replace them if the fix doesn't work?  
yeah you can try out

Author

Commented:
That didn't appear to work.  I removed the nk2 file, opened Outlook and tried to resend and got the same problem.  I did not notice a new nk2 file in the same directory where I removed the old one.  
did you type in the whole email id ? can you send a test mail from someother clients

Author

Commented:
OK, once I closed Outlook and reopened again, I saw the new nk2 file.  Still having the same problem.

Author

Commented:
it works fine from other clients.  I got the email address from their stored contacts.  I'll try typing it in manually after deleting the newer nk2 file.

Author

Commented:
OK, I think I'm making some progress here.  I don't think it has to do with the nk2 file.  I've noticed that when I click the To: button to choose (w/ the original nk2 file) the person's address that is experiencing this problem, I notice that their address says Mail To under email type where just about every single other email type says SMTP.  I found one other contact that said Mail To as well under email type and I got the same error when I emailed that contact.  Any idea on how to change the email type to SMTP?
is this  a contact with external email id configured on exchange? if so then delete the contact and recreate on the exchange box with proper external email id

Author

Commented:
I tried to delete the contact and am unable to.  I'm getting and error message that says The item could not be deleted.  It was either moved or already deleted, or access was denied.  When I sent to make sure the user had permissions to the public folder where the contact resides, I got the following error message from the Exchange system manager:  exchange the requested operation is forbidden c1030af1.  I've been looking online and following Microsoft KB articles and haven't had any luck.  

Author

Commented:
OK, i got my problem figured out.  Apparently all users/computers were denied permissions to access the exadmin directory.  Not sure how that happened.  So I gave the appropriate permissions which allowed me to access the properties of the global address list in exchange system manager.  Once I gave the user permission to delete for that global address list, she was able to delete the contact.  Once I deleted the contact and readded it, problem solved.  Thanks.

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