The problem started when I got a new mac and did a time capsule restore from the old one. I am running parallels with Windows 7 and have Outlook 2013 for Windows on which this feature DOES work properly. Furthermore, I can log into the exchange webmail and this feature also works properly.

Here are troubleshooting steps which I have already tried with no success:

1. Uninstall and reinstall Office 2011

2. Delete all Outlook data from Mac and restore the program.

3. Create new identity in Outlook. 

4. Remove account from Outlook and add back.

5. Delete "Recent Addresses" file from the Outlook directory and rebuild.

6. Remove old identity completely and add a new one.

7. Restored Mac to factory settings and re-install Office.

Basically I am stumped and could use any suggestions to help get this fixed. I am CONSTANTLY sending emails, probably 2000 per day and this is incredibly annoying and destructive to my productivity.

A couple more things that may help someone come up with an answer - The global address book is intact and functional, if I type the first couple letters of an email address and press "TAB" or "ENTER" it will change what I typed to that persons email address. for example, if I type "js" and press tab it will change to "*** Email address is removed for privacy ***." Also, from time to time when I am typing an email address I will see the bottom of the autocomplete drop-down box at the very top of the screen, it is out of view and I can only see one or two names at the bottom and cannot drag it or move it or anything like that but I feel like this may be pertinent information when troubleshooting.