Hi constantm,
Thanks for your updates.
Based on the current situation, I suggest you check if OWA works fine as David suggested first.
If OWA works fine, please do one more test:
Configure this email account in Outlook client in Windows OS and check if the issue persists.
If it works fine, the issue should be related to the Outlook 2011 for MAC. You could try to post this question in the forum below for more professional suggestions.
http://answers.microsoft.com/en-us/mac/forum/macoffice2011-macoutlook?sort=lastreplydate&dir=desc&tab=Threads&status=&mod=&modAge=&advFil=&postedAfter=&postedBefore=&threadType=All&tm=1393902576111
Your understanding is appreciated.
If not, please post it back with more detialed test results for further analysis.
Best regards,
Kid Yang