have to type in full email address every time in order for email to reach user outside my company

I have a user that has one person that was not receiving his email- no kickbacks no messages nothing.  The receiving party's IT person told my user to fully type in the email address and it worked.  The guys email address has a really long domain name so its a pain in the ass to re-type every time.  Can't select from cached email address or even reply to an email from this guy without fully typing in the email address.  I have never heard of this behavior in 20 plus years in IT.

There has to be a better fix for this.

Any ideas or knowledge of this situation?
funkyone60Asked:
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Vasil Michev (MVP)Connect With a Mentor Commented:
Clear the Outlook name cache as explained here: http://support.microsoft.com/kb/287623/en-us
If he is replying to old emails, ask him to fill in the address manually as well. Also make sure that the user doesnt use any predefined entry in the GAL/contact list (or update them with the correct address).
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funkyone60Author Commented:
thank you- solved the issue right away
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