One of my users outlook does not remember the names of the people he has sent too. For example on my outlook when i type in someones name who i've previously sent to it comes up. But with my user it seems to reset itself every day!
Open Contacts by clicking the Open Book icon
Click Tools ->Options->addressing
Half way down you will see a Selection box with a heading "When sending mail, check names using these address lists in the following order". If there is more than one file in this selection box, even though they may have the same name, change the order. The desired file probably needs to be put to the top of the list.
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