You'll only see this on new Macs you enroll? For older Macs already enrolled, they are pre-approved?

I'm coming from 9.101.4 and will upgrade soon.

It would be nice if this showed up for reenrolled Macs too.

Is there any way to trigger this to remind users each day until they do it?

I'm fairly confident this will display for any computer with an MDM profile that is not marked approve so long as they are running 10.13.2 or later and the Jamf Pro server is 10.4 or later.

Good, I've been hoping they would build "conditional access" into Self Service. Add something similar for disk encryption, please! It's really hard to enforce now that users are in control of it.