Thanks for using Outlook.com and for taking the time to provide feedback on the product. We’re currently looking into how we can improve the contact management issues that you’ve reported.
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This is a very annoying problem. Makes for sending the wrong email address tooo often since you have to know which is the current email for someone. Looks like it would be too easy to let you simply delete an old email address that you don't wish to have come up any more. I gave up on facebook because I wasn't clarvoint. This has been a festering problem for a long time. Once I spent an hour deleting old email addresses that were no longer used. Well guess what they are all still there. You would think that a computer software company could at least make this part work.