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Get Bounce back Undeliverable when trying to use autocomplete list in Outlook2013,but not when using the address book

Ok so we have a user who we upgraded from Outlook 2010 to Outlook 2013 and when he uses his auto-complete list to select a user and tries to send an email to say for example c.killer21@gmail.com he gets a bounce back undeliverable, but when he goes to his address book and selects the same user which has the same exact email address the message goes through and he doesn't get a bounce back. Now keep in mind this his only with a few email addresses in his auto-complete list. Also, just so you guys have a little background info, the user works for a company that pays for hosted exchange through a company called intermedia and the hosted server is running exchange 2007. Please help don't get why this would be happening.

Thanks,
Corey Kidder
corey@creativenetworks.net
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Seth Simmons
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I tried to do that. I started to type the email address then as it showed up in the list i deleted it. It got deleted it,but when I went to go manually type the email address in and sent a test message out it didn't populate in the list and I still received a bounce back of undeliverable. Weird stuff.

Thanks,
Corey
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