This is only a short blog post to document a solution for a very annoying problem. After the automatic update of my Outlook to the latest Office 365 build (version 1809), it has started to prompting for credentials. I’m using Outlook to access a Microsoft Exchange 2016 server (on-premises), without any hybrid configuration. A pretty simple and plain Exchange 2016 on-prem deployment. I knew, that it has to be related to Office 365, because the Outlook 2016 on my PC at the office was not affected.