I recently set up Office 365 Business Premium. Still on the trial but I'm planning to stay
Autodiscover is not working against Outlook 2011 for Mac (v14.1.0 i.e. SP1)
It does reliably work against Outlook 2010 and Outlook 2013 on Windows from the same site.
In the Office 365 control panel, the domain setup says there are no issues and my autodiscover.mydomain.com CNAME points to autodiscover.outlook.com as required.
On the Mac I get the warning about the redirect to https://autodiscover-s.outlook.com/autodiscover/autodiscover.xml so I'm presuming the DNS is all OK to even get that far (and obviously works with Windows Outlook).
Using the Connectivity tester everything is successful although there is a warning on the SSL certificate
Attempting to test potential Autodiscover URL https://autodiscover-s.outlook.com/Autodiscover/Autodiscover.xml
...
Testing the SSL certificate to make sure it's valid.
The certificate passed all validation requirements.
...
Certificate trust is being validated.
The certificate is trusted and all certificates are present in the chain.
Analyzing the certificate chains for compatibility problems with versions of Windows.
Potential compatibility problems were identified with some versions of Windows.
Additional Details
The Microsoft Connectivity Analyzer can only validate the certificate chain using the Root Certificate Update functionality from Windows Update. Your certificate may not be trusted on Windows if the "Update Root Certificates" feature isn't enabled.
Elapsed Time: 3 ms.
This doesn't appear to be a problem for any Windows machines I've tried.
Username/password are absolutely correct since I've used them in the web interface and other Windows installations I've tested.
After the redirect warning it just drops out to "Account cannot be added. Note that Outlook 2011 requires Exchange Server 2007 SP1 Update Rollup 4 or later". I've noticed that with SP1 of Outlook once it fails it disables the "Configure automatically" option so the only way to retry is
This is about where any of the help, guides and other threads I've found drop out. Check CNAME, check username/password and that's about it.
The Mac is a brand new clean install of Yosemite with simply Office 2011 + SP1 installed.
Any ideas? I previously had this working with another hosted Exchange provider and didn't have such a problem (I also didn't have the SSL certificate issue either).
Thanks
Christian