We have recently seen an issue with autodiscover email settings not properly working when using Windows 10, Outlook 2016, and Office365.
As you are no longer able to manually configure your email server settings with the latest versions off Outlook 2016 as we did with earlier versions of Outlook, we needed to get to the bottom of this issue once and for all.
It seems that in our case autodiscover simply hung and failed at every attempt.
The solution for our case:
Add the following Dword values in the client pc’s registry:
HKEY_CURRENT_USER\SOFTWARE\Microsoft\Office\16.0\Outlook\AutoDiscover\ExcludeHttpsAutoDiscoverDomain = 1
After a quick reboot, Outlook autodiscovery instantly succeeded and connected as designed.