Outlook 2010 and 2013 for Windows allow whitelisting of redirected autodiscover servers, which will prevent users from being presented with an "Outlook was redirected to the server <server fqdn> to get new settings for your account..." warning. https://support.microsoft.com/en-us/kb/2480582 An equivalent function in Office 2016 for Mac would be very useful. Personally I would expect to see the list stored in the user's Outlook preferences .plist.
Jonathan Guerin commented
Further to the details above, the user is not equipped to make this kind of decision. The mail server should know what autodiscover domains it trusts and use those. The dialog that is presented to the user does not allow them to make an appropriate security decision, given that they just want to access their email, and the dialog is preventing from doing so.
It's very much against security best practices - don't let the user makes security choices that blocks access to their workflow without being very clear why you are doing so.
Please help add a method to suppress the autodiscover warning dialog.
As mentioned at below post, the remember server settings is not working for sharing calendar scenario. You will always get a prompt even after you check the checkbox to "always rememer this server".
I was able to disable autodiscovery so that my setup would stop flipping between our internal and external mail servers by following the guide at: https://stackengineer.com/macos/disable-exchange-autodiscover-outlook.html
Please add an AppleScript command for whitelisting specific autodiscovery URLs.
Outlook 2016 needs to have the autodiscover issue when a user's email and the domain are hosted on different servers resolved. Just telling a user to accept a certificate that is mismatched is not a habit user's need to be encouraged to do and having to cancel the the certificate check every time Outlook opens up is not a solution either.