Hello!
I had Office 365 working fine with all of my systems when I had a SBS 2011 domain. I finally made the switch to Server 2012 Essentials domain (fresh installation). I removed all workstations from the SBS 2011 domain, turned off the SBS 2011 server, installed the fresh 2012E server, rebooted the workstations, joined everything to the domain, and everything works fine EXCEPT for Office 365. NO system would connect Outlook to any account, always getting an error stating, "An encrypted connection to your mail server is not available." It failed even with an unencrypted attempt. Not my Win 7 physical system running Office 2007, not a Win 7 VM running Office 2010, not a Win 8 VM running Office 2013, not Win 8 running Office 2007, nothing worked, and they all worked fine in the SBS 2011 domain.
During six hours or so of troubleshooting, I tried disabling and re-enabling 365 integration in 2012E, testing autodiscover, turning off AV and Windows firewall, etc, yet always got the same error from Outlook. I started wondering if 2012E was interfering. In the 2012E dashboard on the Users tab, I double-clicked a user and then clicked on the Office 365 tab. After a few minutes, it would fail and give an error about checking the Internet connection.
On a whim, I shut down the 2012E server, changed my local computer to use 4.2.2.2 for DNS, and BINGO, Outlook configured the account. I did it on a few systems.
I then restarted the 2012E, disabled Office 365 integration, and tried again, using the 2012E as the DNS as normally done in an AD domain. Systems could not configure Outlook. I next tried leaving the 2012E server running, but changed the DNS on local systems to 4.2.2.2, and they also were able to configure Outlook.
SOMETHING in Server 2012E is stopping the workstations form finding Office 365 properly.
What could it be?
Gregg Hill