So it appears that something has changed in the way Outlook for Mac connects to Exchange between 20.
After a while, I'll see a '!' in the lower right and when I click on that, I'll see a -18599 error message. Now if I close Outlook and restart it, I get the exact same message in 7 above. Now if I compose a new email and attempt to send it, I the "Sending." status with a blue progress bar in the bottom middle of the screen and the email never gets sent. I do see all of my emails but it is no longer connected. In the lower right corner of the main Outlook window it says "Connecting to: xyz". After a minute or so, I then notice that the little dot turns back to yellow. At this point, I start seeing emails populate my inbox and the little dot next to the account I just created turns from yellow to green and it looks like everything is working properly. Do you want to continue? I click Continue. I then get this message: A secure connection cannot be established with the server xyz.com because its intermediate or root certificate cannot be found. I enter the email server name (same one I used in Outlook 2011 which worked) and click Add Account. I uncheck the "Configure automatically" checkbox. I enter my Exchange email address, leave the Method as "User name and Password" and enter my User name (domain\username) and password. I click on the +v button at the bottom and select Exchange. I go into Outlook=>Preferences=>Accounts. I start Outlook 2016 which doesn't have an Exchange account. 
Office 2016 brings welcome uniformity by making the Mac version nearly identical to the Windows version.
#Upgrade from office for mac 2011 to 2016 upgrade
Here is what I've tried and what I'm seeing: Office 2016 is a much welcome upgrade for any existing Office installation, particularly for Mac users who’ve been suffering under the rather awful Office 2011 with its ugly, clunky interface. After upgrading my Macbook Pro which runs OSX 10.10.5 (Yosemite) from Office 2011 to Office 2016, I am no longer able to connect to my Exchange 2010 corporate mailbox.
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