I have one user in my environment who is on an iMac 2011. After multiple issues with Outlook and Exchange on this machine, I am testing on a spare just like his to find a solution. I have been at this issue for over 2 weeks now! The test machine was wiped and I have done a clean install of El Capitan 10.11.4. When I set up his Outlook (Keep in mind we are using an archaic Exchange version - 2010 SP1). The Outlook account sets up just fine. About halfway through syncing, however, it stops and I cannot get it to complete. I have set it to push regularly and he has no problem on his iphone, tablet, or webmail. It is definitely the desktop client. Any suggestions (quickly, please!) are welcome! BTW, Microsoft Office for Mac 2011 is completely up to date - 14.6.3