Does ISPConfig support autoconfig and autodiscover for Outlook 2016, 2019 etc out of the box, or is there a special configuration available to enable auto-configuration of new Outlook clients?
I'm not very knowledgeable in Outlook specifics, but check out https://schaal-it.com/ispconfig-automail/ and see if it will meet your needs. It is easy to setup.
I'm using this and I can confirm this is easy to set up and it works like a charm. If you use HSTS for your domains, don't apply IncludeSubDomains, because otherwise clients won't be able to connect securely.
