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Users gets sporadic System Undeliverable messages from good email addresses


I'm getting backed into a corner with a user we have that is running into more and more problems with sending emails outside our company organization.  This seems to be completely sporadic.  It is only happening on external contacts.  Hes tried to directly type the email address in, click on mailto links, find them in directories, and nothing seems to make a difference.  The message that almost instantly comes back is the following:

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

      Subject:      Meeting at Company
      Sent:      9/26/2012 9:02 AM

The following recipient(s) cannot be reached:

      'email@externaldomain.com' on 9/26/2012 9:02 AM
            None of your e-mail accounts could send to this recipient.

Why does this keep happening, and what do i do to correct it?

Thanks everyone!

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8/22/2022 - Mon
Justin Yeung

do you have mail delivery restriction enabled under mail flow settings of the contacts?

can you also verify that the "external domain name MX record with an correct IP address" can be resolved on your network?

is it happening to only 1 user that sent or entire company are having the same issue sending to the "contacts"

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It is only happening to one user.  I haven't had any reports of anyone else seeing the issue.  its just this one user.

I will clear the auto complete, and make sure that cached mode is disabled, I'll post back the outcome of these in a few days, cause like I said, once I make the change, it could be an hour, or a week before he sees the error again...

I'll touch base with you all soon, thank you for the suggestions!
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OK, I have disabled the cached mode, and I have wiped the nk2 file for outlook 2010.  I am going to let it go for a while and see if the issue pops up again.  I also verified there are no sending restrictions on the user settings in Exchange.  Thanks for the suggestions!

I'll post back in a few days to let you all know if its working or not :)

Thank you!
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