For this discussion I will substitute the real domain name with myclient.com External URL for the Exchange server is exchange.myclient.com. Remote Connectivity Analyzer for Outlook Anywhere passes with flying colors. But when I attempt to autoconfigure Outlook I get the certificate warning that is associated with URL myclient.com. This URL belongs to MyClient web site, and the certificate that Outlook complains about is the one associated with the web site. Why is this happening? Outlook is supposed to find URL exchange.myclient.com not myclient.com. I checked the settings multiple times, and don't forget that Analyzer isn't compaining. Any ideas?

Hello, When you need Autodiscover to work, these are needed: 1.autodiscover.domain.com must be resolved from Internet. 2.autodiscover.domain.com must be included in the certificate which is enabled in Exchange IIS. You can check whether the autodiscover.domain.com is included in your certificate. Thanks, EvanEvan Liu TechNet Community Support

Thanks for your reply. However, this seems a bit deeper. I have checked and double-checked the usual suspects. AUTODISCOVER.DOMAIN.COM is resolved and is included in the certificate. If it wasn't, Connectivity Analyzer would fail in its early stages. Yet it passes the test COMPLETELY. But when I try to autodiscover with Outlook, that when the problem rears its head.

Autodiscover will search the following locations: https://<domain>.com/autodiscover/autodiscover.xml as well as https://autodiscover.<domain>.com/autodiscover/autodiscover.xml You will probably find that you have an SSL enabled site at https://<domain>.com which isn't actually your exchange server, or possibly even on your domain, and autodiscover is either failing to reach /autodiscover/autodiscover.xml at that location or the SSL certificate in use isn't a 3rd party certificate.Network Manager, Evergreen Catholic Schools

Relseh, you are correct this exactly what's happening. But why is it going to DOMAIN.COM to connect to Outlook Anywhere? This late in the process it should have already gotten the correct URL, which in my case is EXCHANGE.DOMAIN.COM. Remember Connectivity Analyzer goes through all the stages with no problem.