Forum Discussion
Outlook prompts for password using ADFS 3.0
This is set on ADFS: Enable-AdfsEndpoint -TargetAddressPath “/adfs/services/trust/13/windowstransport”
When I use the hosts file on a workstation to point autodiscover to autodiscover.outlook.com everything is working as expected, with SSO experience, not asking for a password.
So I think the behavior is caused because autodiscover points to our on-prem Exchange server and during the autodiscover process it hits this server first. But I cannot find an article which agrees with my thought, or a solution/ workaround for this.
It should be the expected behavior in hybrid setup. Autodiscover will and should point to your on-premises Exchange setup.
This article here talks about the autodiscover lookup process in detail: https://blogs.technet.microsoft.com/rmilne/2015/04/29/office-365-autodiscover-lookup-process/
It is because of the autodiscover cache which points the client to the old Exchange 2010 server. When I delete the autodiscover cache (manually) from the users profile and reboot the device I don`t see the basic auth popup and the user is logged on seamless to Outlook.
I have also setup a few test users on the Exchange 2016 server, when they are moved to Office 365, they don`t see the popup, just restart Outlook and they are logged on to Outlook.
So when I move users at night and the next morning the users starts his device, the autodiscover cache should be renewed and don`t see a popup.