Exchange bounce backs preventing email being sent


SBS2003 with Exchange 2003
Win7 with Outlook 2010 x64
Brand new PC and user which has only just entered the environment about 2 weeks ago.
No other user is having this problem.

I have a user who intermittantly has trouble sending external emails. This has happened before to a different external user and the solution was to remove that email address from the NK2 file and reenter manually. I assume the NK2 was corrupt in some way.

however this has now happened again to an external user, of which this is the first email ever to be sent to them by this user ie NK2 cannto be interfering.

There are no rules on the Exchange box to prevent him sending this email.

any thoughs anyone?

Subject: Undeliverable: 40 receptions
Your message did not reach some or all of the intended recipients.
      Subject:  40 receptions
      Sent:     29/03/2012 12:00
The following recipient(s) cannot be reached:
      '' on 29/03/2012 12:00
            None of your e-mail accounts could send to this recipient.
Gareth McKeeCEO/OwnerAsked:
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WORKS2011Managed IT Services, Cyber Security, BackupCommented:
I would start by doing an nslookup on domain you'll probably find that DNS can't resolve the name. If it doesn't resolve do ipconfig /flushdns on the server and it doesn't hurt to scavenge stale records on the DNS server as well, try nslookup again, if it was failing and now doesn't you should be able to send the email.
Gareth McKeeCEO/OwnerAuthor Commented:
Hi Works,

thanks for input.

the user forwarded the email to a colleague who was immediately able to email it to the same external user, but I will try your ideas and get back asap.

WORKS2011Managed IT Services, Cyber Security, BackupCommented:
are you sure, check the queue it could be sitting in the sever queue and he believes the email was sent, it won't be returned to the sender until the queue expires.

Did nslookup resolve to ip?
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Gareth McKeeCEO/OwnerAuthor Commented:
Hi Works,

have completed the test and the NSlookup is working correctly.

nothing in the queues.

WORKS2011Managed IT Services, Cyber Security, BackupCommented:
I would go into the users Outlook and delete the contact, make sure to delete the cached one as well. Test by retyping the email address in question. Sounds like problem is coming from the users Outlook. I've seen where the contact is corrupt which can cause this, especially since its not having a problem on the domain / server level.
Gareth McKeeCEO/OwnerAuthor Commented:
I agree this is very strange.

To clarify this was not a contact in Outlook and was the first time the email address had been entered into Outlook, I therefore discount the corrupt NK2 file issue.

This happened about 2 weeks ago with a different external client which had been previously emailed. I removed the offending email from the autocomplete in Outlook, had the user reenter manually and all worked. Thus believing the corrupt/slightly corrupt NK2 was to blame.

Now I am not so sure as the email address had not previously been used.

What are your thoughts on this?
WORKS2011Managed IT Services, Cyber Security, BackupCommented:
I would test with OWA and Outlook this should isolate the problem down to server side or Outlook / workstation. Your thoughts?

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Gareth McKeeCEO/OwnerAuthor Commented:
ooohhhhh, interesting. Yep, I will give this a go.
Gareth McKeeCEO/OwnerAuthor Commented:
This did narrow it down to the PC, created a new profile and this seems to have fixed the issue.
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