Using older versions of Outlook for Mac in business environments
Had this problem on my Mac Air with Outlook 2011. Solved the problem but it was a server-side solution.
Had to rebuild the virtual directories on the Exchange Server 2010, apparently that's a known problem. In order to do that thru the Exchange Management Console had to upgrade the server to SP3. Then could use the GUI to rebuild each of the IIS virtual directories.
That solved it!