Forum Discussion
Re: Outlook prompts for password using ADFS 3.0
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/
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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.
