We recently Upgraded from Entourage 2008 to Outlook for Mac 2011. Migration went fine for all 50 users. I went to replace one users mac and the new mac gives this error. I have noticed 2 other desktops I just setup are also giving this error. No laptops I just setup are giving this error. All macs use the same image regardless if they are a laptop or desktop. 

I found in another thread on here to uncheck use SSL. Everyone has this checked.
I also found something server side. If it was server side wouldn't everyone be having this issue?

I'm puzzled.