Hi Bwhoward88,
Does this issue occurs to other users in your tenant? If you are alone Administrator or user try to create Test Users and check it for them.
Meanwhile, please configure this profile in Outlook 2010 and share the result whether any improvement?
However, you can configure multiple accounts in Outlook 2013 and check it for vice versa for another users. For more information about configure multiple accounts, see http://technet.microsoft.com/en-us/library/ee815819.aspx
Best Regards,
Pratik Pandya