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I have sometimes deleted an email address from Microsoft Outlook when a friend informs me that they have a new email address. However, when I attempt to send an email thereafter to that person--I am presented with a box which requires me to choose an email address--and it presents the old, deleted email address and the new one I have entered. Sometimes I have forgotten which is the new email address--so--is there anyway to permanently remove an email address, so that I am not presented with the 2 options each time?
 

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You are talking about the auto-complete feature of Outlook. You can remove entries from this list. When you are presented with the list of addresses to choose from use the up\down arrow keys on your keyboard to highlight the address you no longer want. Once that address is highlighted press the "delete" key on the keyboard and the address will be permanently removed.
 
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