It seems that Exchange 2010 Update Rollup 26 has broken EWS functionality with Outlook 2016 and Outlook 2019. This appears to be causing continuous password prompts for some users in Outlook 2016 & 2019. Analyzing the traffic with Fiddler shows a 500 error accessing the EWS URL with Outlook 2016. Further inspection of the EWS traffic shows the error "The specified server version is invalid" when using Outlook 2016. Outlook 2013 does not seem to have an issue, and the traffic does not show this error, it shows the version number that is returned from the server, MajorVersion="14" MinorVersion="3" MajorBuildNumber="442" MinorBuildNumber="0" Version="Exchange2010_SP2."