Today we released an updated version of the Exchange Remote Connectivity Analyzer. For those of you not familiar with this site, it is a Web-based tool that helps you troubleshoot connectivity issu...
Updated Jul 01, 2019
Version 2.0
Blog Post
Hey Sejong,
Part of the Autodiscover process will try to connect to https://domain.com/autodiscover/autodiscover.xml
https://domain.com/autodiscover/autodiscover.xml, but many times this is *expected* to fail with a cert name mismatch - the Outlook client also moves past this. Typical deployments are with a wildcard or UC certificate with multiple names on the certificate.
So you'd probably have: autodiscover.domain.com and mail.domain.com on the certificate. Test-OutlookWebServices is just using the InternalUrl or ExternalUrl values provided from the WebServicesVirtualDirectory. You can run "Get-WebServicesVirtualDirectory
| fl *url" in the Management Shell to view these values. These also can be changed via Set-WebServicesVirtualDirectory. You should probably check out the Autodiscover Whitepaper or post in the appropriate TechNet forum for more info.
Brad