Is autocomplete enabled? Look in tools, options, email options, advanced...
near the bottom of the dialog is the Suggest names option. It should be
checked.
Is outlook closing properly? Does it remember any names when you send to
someone multiple times during one session? The file is not saved until
outlook closes and if it doesn't close properly, its not saved. Addresses
you've sent to once during the session should come up during the session if
its enabled in tools, options.
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Diane Poremsky [MVP - Outlook]
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Poll: What version of Outlook do you use?
http://forums.slipstick.com/showthread.php?t=27072