I just installed a new Exchange 2016 server in an office. It is standalone, so no one is domain joined, all use Outlook Anywhere to connect with Outlook 2016. Certificates have the outside domain, and everything works well, except we cannot share contacts folders or calendars, unless our network adapters point the DNS to the exchange server. We can then share contacts and calendars. However, when we do that, we get a certificate alert when starting Outlook, which states that the cert is good, it’s valid, it’s 3rd party, but the server name is different. It shows that the local computer server name is different from the domain name (autodiscover.domain.com vs exchangesvr.local). I’ve tried installing the cert, but it always displays that error.
The internal autodiscover URI is pointed to the external name autodiscover.domain.com.
How can I fix this? If I point the Network adapter DNS to the router, or external DNS everything works fine except the sharing, if I point DNS to the exchnge server, I get the cert warning. A bit of a Catch-22!