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I am looking at updating our Certificate Servers from 2008 to 2016 which I partly have built out or to 2019.  Are there any new features out now or in the future that would make since for me to restart with 2019 server instead?

I wasn't able to get any documentation yet on new features for ADCS, so I don't think there are any major new features. That said, as a CA is usually long-lived, you might still want to consider building it out with Server 2019

Quadrotech - Management, Reporting and Migration for Office 365

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