So my organization is transitioning to Office365 for our company email due to its many advantages (continuous uptime and less overhead in general), but we still have internal company websites that run on our SBS.
I've shut down the services for the exchange on the SBS, but I do not want to remove the exchange role from it, since it's an archive of our existing mail at this point, and should we decide not to go with a hosted solution in the future, I could load mail back into it.
I can get the Outlook clients to connect to Office365 if I point to external DNS, but if I use internal DNS, I have various irregularities. One outlook client connects fine, another prompts for my Office365 password when it starts... and the third throws a cert error (the SBS has an expired cert) and asks for credentials to my SBS server... It never gets out of our organization.
I've set an autodiscover CNAME record for autodiscover.outlook.com and autodiscover-s.outlook.com. We're using Outlook 2013 with only one profile on it - the profile for the Office365 server. We configured the profile when on external DNS, so we're sure that the Office365 server is the home mailbox and that it hasn't somehow gotten confused and used our internal exchange box.
Any thoughts as to how I can get Outlook to synchronize correctly without mangling or decommissioning my SBS?